过渡金属催化的含氮、氧杂环化合物的合成方法学研究
|
摘要
过渡金属参与的环化反应是合成杂环化合物的有效方法,这种方法往往能够在温和的条件下,从简单易得的原料出发,高选择性地合成杂环分子。过渡金属铁或铜试剂因其具有高催化活性,价格低廉,环境友好等特点而逐渐被化学家们所关注。本论文围绕着铁或铜参与的杂环化合物的合成而展开,包括以下五部分内容：
1.通过氯化亚铜催化的炔,醛,胺的三组分偶联反应,“一锅法”合成了1,4-苯并恶嗪类化合物。炔,醛,胺的三组分反应提供了一种合成炔丙胺的简便方法,通过在芳胺的邻位引入氧亲核反应位点,使其对生成的炔丙胺的碳-碳三键发生环加成反应,实现了“一锅法”进行的串联偶联/环化反应。该方法能够高选择性地合成Z型的N-烷基,烯丙基以及苄基取代的1,4-苯并恶嗪类化合物,收率为30%-85%。
2.通过三氯化铁催化的2-炔丙基酚的分子内氧-氢键对碳-碳三键的加成反应合成了2H-1-苯并吡喃类化合物。实验结果表明：不同的添加剂对反应结果有较大影响,当苯胺作添加剂时,主要生成endo-dig型环化产物；当正丁胺作添加剂时,则主要生成exo-dig型环化产物。反应的选择性受底物的影响较大,当炔丙位和炔位同为芳基取代的底物反应时,选择性较高,大多数底物能够单一生成苯并吡喃类化合物,其他的底物则以87：13至95：5的选择性得到苯并吡喃和苯并呋喃的混合物。通过这种方法合成了15个苯并吡喃衍生物,收率为23%-80%。
3.通过微波促进的三氯化铁催化的酚的苄基化/环化反应能够很方便地合成9-取代氧杂蒽类化合物。在苄基化试剂的芳环邻位引入卤素取代基,能够使其在与酚发生苄基化反应之后,继续发生分子内串联反应,形成环化产物,以38%-77%的收率合成了9-烷基以及9-芳基取代的氧杂蒽衍生物。现有的文献所报道的氧杂蒽的合成方法中,较少涉及9-烷基取代氧杂蒽的合成。不仅邻溴代苄基乙酸酯,其他的苄基化试剂,邻溴代苄溴以及邻溴代苄基碳酸酯也都能够较好地反应。
4.中氮茚是一类重要的氮杂环化合物,许多中氮茚衍生物具有良好的生物医药活性。通过Pd/Cu催化的2-溴吡啶与炔丙基醚的偶联／环异构化反应合成了3-含氧取代中氮茚类化合物。该方法的优点是无需分离环化产物前体,而是“一锅法”串联进行的,提高了反应效率。
5.铜试剂能够催化3-(2-吡啶基)炔丙胺的自身双分子环化成中氮茚的反应。该方法使用碘化亚铜作催化剂,碳酸铯作碱,DMA溶剂中100℃反应,就能够以中等的收率很方便地合成2-烯基取代中氮茚类化合物。据我们所知,2位带有烯基取代的中氮茚类化合物还未见有报道。
通过以上这些方法,总共合成了8个1,4-苯并恶嗪化合物,15个2H-1-苯并吡喃化合物,14个氧杂蒽以及21个中氮茚化合物,并通过了1HNMR,13CNMR及质谱表征。
Transition metal-mediated cyclization is one of the most attractive methodologies to synthesize heterocyclic compounds. It can construct complex molecules from readily accessible starting materials under mild conditions with high selectivity. Iron and copper have drawn much attention in organic synthetic chemistry due to their unique properties, such as low price, less toxicity and easy of synthesis. This thesis is focused on the synthesis of heterocyclic compounds catalyzed by iron or copper, including the following five parts:
1. An efficient one-pot procedure for the preparation of 1,4-benzoxazine derivatives through copper-catalyzed three-component couplings was reported. The three-component coupling of aldehydes, amines and alkynes (A3 coupling) was a convenient method towards propargylamines. Arylamines with an ortho-oxygen nucleophile can also be employed in the A3 coupling reaction, and a sequential intramolecular nucleophilic attack of the oxygen to the triple bond furnished the benzoxazine derivatives in one-port. N-methyl, N-allyl and N-benzyl substituted 1, 4-benzoxazine derivatives were obtained in a high regio- and stereo selectivity manner with the yields from 30% to 85%.
2. Iron-catalyzed high regioselective intramolecular O-H addition across C-C triple bond to affod 2H-1-benzopyran derivatives was described. Different additives could effect the reaction significantly. The use of aniline give 2H-1-benzopyran derivatives as the main products, while the use of butan-1-amine give benzofuran derivatives as the only products. The substrates with two aryl groups at the propargylic position and the triple bond terminus could afford the corresponding 2H-1-benzopyran derivatives with higher selectivity. In many cases, the 2H-1-benzopyran derivatives were the only product, others afforded a mixture of benzopyran and benzofunan with the selectivity from 87:13 to 95:5.
3. Xathenes could be efficiently prepared using iron-catalyzed, microwave-promoted cascade benzylation-cyclization of phenols. Through the introd ucing of an ortho-halogen substitute to the benzylating reagents, a cascade benzylation/cyclization catalyzed by FeCl3 occurred to give xanthene derivatives in one port with the yields from 38% to 77%. And a variety of benzylating reagents such as benzyl acetates, benzyl bromides, and benzyl carbonates could afford 9-substituted xanthene derivatives conviently, especially 9-alkyl xanthenes, which were difficult to synthesize according to the reported methods.
4. lndolizines are important nitrogen-containing heterocyclic compounds and many of them display important biological activities. Through Pd/Cu-catalyzed coupling/cycloisomerization reaction of 2-bromopyridine with propargyl ether, 3-substituted indolizines could be synthesized in one-pot. The reaction was carried out in a tandem manner without isolation of intermediates, 8 desired compounds were synthesized.
5.2-allylsubstitued indolizines were obtained conviently through copper-catalyzed cyclic isomeriation/nucleophile addition of (3-(pyridin-2-yl) prop-2-ynyl) amine. The best condition was to use CuI as catalyst, Cesium carbonate as base, DMA as solvent. Under this condition, the desired products were obtained in 33%-68% yields, and there are no reports for the preparation of 2-allylsubstituted indolizines, to the best of our knowledge.
In this thesis,8 designed 1,4-benzoxazine derivatives,15 designed 2H-1-benzopyran derivatives,14 designed xanthene derivatives, and 21 designed indolizines were synthesized. All compounds were characterized by 1H,13C NMR spectroscopy and mass spectroscopy.
1.通过氯化亚铜催化的炔,醛,胺的三组分偶联反应,“一锅法”合成了1,4-苯并恶嗪类化合物。炔,醛,胺的三组分反应提供了一种合成炔丙胺的简便方法,通过在芳胺的邻位引入氧亲核反应位点,使其对生成的炔丙胺的碳-碳三键发生环加成反应,实现了“一锅法”进行的串联偶联/环化反应。该方法能够高选择性地合成Z型的N-烷基,烯丙基以及苄基取代的1,4-苯并恶嗪类化合物,收率为30%-85%。
2.通过三氯化铁催化的2-炔丙基酚的分子内氧-氢键对碳-碳三键的加成反应合成了2H-1-苯并吡喃类化合物。实验结果表明：不同的添加剂对反应结果有较大影响,当苯胺作添加剂时,主要生成endo-dig型环化产物；当正丁胺作添加剂时,则主要生成exo-dig型环化产物。反应的选择性受底物的影响较大,当炔丙位和炔位同为芳基取代的底物反应时,选择性较高,大多数底物能够单一生成苯并吡喃类化合物,其他的底物则以87：13至95：5的选择性得到苯并吡喃和苯并呋喃的混合物。通过这种方法合成了15个苯并吡喃衍生物,收率为23%-80%。
3.通过微波促进的三氯化铁催化的酚的苄基化/环化反应能够很方便地合成9-取代氧杂蒽类化合物。在苄基化试剂的芳环邻位引入卤素取代基,能够使其在与酚发生苄基化反应之后,继续发生分子内串联反应,形成环化产物,以38%-77%的收率合成了9-烷基以及9-芳基取代的氧杂蒽衍生物。现有的文献所报道的氧杂蒽的合成方法中,较少涉及9-烷基取代氧杂蒽的合成。不仅邻溴代苄基乙酸酯,其他的苄基化试剂,邻溴代苄溴以及邻溴代苄基碳酸酯也都能够较好地反应。
4.中氮茚是一类重要的氮杂环化合物,许多中氮茚衍生物具有良好的生物医药活性。通过Pd/Cu催化的2-溴吡啶与炔丙基醚的偶联／环异构化反应合成了3-含氧取代中氮茚类化合物。该方法的优点是无需分离环化产物前体,而是“一锅法”串联进行的,提高了反应效率。
5.铜试剂能够催化3-(2-吡啶基)炔丙胺的自身双分子环化成中氮茚的反应。该方法使用碘化亚铜作催化剂,碳酸铯作碱,DMA溶剂中100℃反应,就能够以中等的收率很方便地合成2-烯基取代中氮茚类化合物。据我们所知,2位带有烯基取代的中氮茚类化合物还未见有报道。
通过以上这些方法,总共合成了8个1,4-苯并恶嗪化合物,15个2H-1-苯并吡喃化合物,14个氧杂蒽以及21个中氮茚化合物,并通过了1HNMR,13CNMR及质谱表征。
Transition metal-mediated cyclization is one of the most attractive methodologies to synthesize heterocyclic compounds. It can construct complex molecules from readily accessible starting materials under mild conditions with high selectivity. Iron and copper have drawn much attention in organic synthetic chemistry due to their unique properties, such as low price, less toxicity and easy of synthesis. This thesis is focused on the synthesis of heterocyclic compounds catalyzed by iron or copper, including the following five parts:
1. An efficient one-pot procedure for the preparation of 1,4-benzoxazine derivatives through copper-catalyzed three-component couplings was reported. The three-component coupling of aldehydes, amines and alkynes (A3 coupling) was a convenient method towards propargylamines. Arylamines with an ortho-oxygen nucleophile can also be employed in the A3 coupling reaction, and a sequential intramolecular nucleophilic attack of the oxygen to the triple bond furnished the benzoxazine derivatives in one-port. N-methyl, N-allyl and N-benzyl substituted 1, 4-benzoxazine derivatives were obtained in a high regio- and stereo selectivity manner with the yields from 30% to 85%.
2. Iron-catalyzed high regioselective intramolecular O-H addition across C-C triple bond to affod 2H-1-benzopyran derivatives was described. Different additives could effect the reaction significantly. The use of aniline give 2H-1-benzopyran derivatives as the main products, while the use of butan-1-amine give benzofuran derivatives as the only products. The substrates with two aryl groups at the propargylic position and the triple bond terminus could afford the corresponding 2H-1-benzopyran derivatives with higher selectivity. In many cases, the 2H-1-benzopyran derivatives were the only product, others afforded a mixture of benzopyran and benzofunan with the selectivity from 87:13 to 95:5.
3. Xathenes could be efficiently prepared using iron-catalyzed, microwave-promoted cascade benzylation-cyclization of phenols. Through the introd ucing of an ortho-halogen substitute to the benzylating reagents, a cascade benzylation/cyclization catalyzed by FeCl3 occurred to give xanthene derivatives in one port with the yields from 38% to 77%. And a variety of benzylating reagents such as benzyl acetates, benzyl bromides, and benzyl carbonates could afford 9-substituted xanthene derivatives conviently, especially 9-alkyl xanthenes, which were difficult to synthesize according to the reported methods.
4. lndolizines are important nitrogen-containing heterocyclic compounds and many of them display important biological activities. Through Pd/Cu-catalyzed coupling/cycloisomerization reaction of 2-bromopyridine with propargyl ether, 3-substituted indolizines could be synthesized in one-pot. The reaction was carried out in a tandem manner without isolation of intermediates, 8 desired compounds were synthesized.
5.2-allylsubstitued indolizines were obtained conviently through copper-catalyzed cyclic isomeriation/nucleophile addition of (3-(pyridin-2-yl) prop-2-ynyl) amine. The best condition was to use CuI as catalyst, Cesium carbonate as base, DMA as solvent. Under this condition, the desired products were obtained in 33%-68% yields, and there are no reports for the preparation of 2-allylsubstituted indolizines, to the best of our knowledge.
In this thesis,8 designed 1,4-benzoxazine derivatives,15 designed 2H-1-benzopyran derivatives,14 designed xanthene derivatives, and 21 designed indolizines were synthesized. All compounds were characterized by 1H,13C NMR spectroscopy and mass spectroscopy.
引文
1. For reviews, see:(a) Bolm, C.; Legros, J.; Paih, J. L.; Zani, L. Chem. Rev.2004, 104,6217. (b) Correa, A.; Mancheno, O. G.; Bolm, C. Chem. Soc. Rev.2008,37, 1108. (c) Sherry, B. D.; Furstner, A. Acc. Chem. Res.2008,41,1500.
2. (a) Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jφrgensen, K. A., Eds.; Wiley-VCH:Weinheim,2002. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev.1996,96,635.
3. Lautens, M.; Klute, W.; Tam, W. Chem. Rev.1996,96,49.
4. Morandi, B.; Carreira, E. M. Angew. Chem. Int. Ed.2010,49,938.
5. (a) Hamaker, C. G.; Mirafzal, G. A.; Woo, L. K. Organometallics 2001,20,5171. (b) Edulji, S. K.; Nguyen, S. T. Organometallics 2003,22,3374.
6. Ohara, H.; Itoh, T.; Nakamura, M.; Nakamura, E. Chem. Lett.2001,624.
7. Rosenblum, M.; Scheck, D. Organometallics 1982,1,397.
8. Bouwkamp, M. W.; Bowman, A. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Chem.2006,128,13340.
9. Taniguchi, T.; Ishibashi, H. Org. Lett.2010,12,124.
10. Cantagrel, G.; de Carne Carnavalet, B.; Meyer, C.; Cossy, J. Org. Lett.2009,11, 4262.
11. (a) Breschi, C.; Piparo, L.; Pertici, P.; Caporusso, A. M.; Vitulli, G J. Organomet. Chem.2000,607,57. (b) Funhoff, A.; Schaufele, H.; Zenneck, U. J. Organomet. Chem.1988,345,331. (c) Usieli, V.; Victor, R.; Sarel, S. Tetrahedron Lett.1976, 2705. (d) Hubel, W.; Hoogzand, C. Chem. Ber.1960,93,103.
12. Breschi, C.; Piparo, L.; Pertici, P.; Caporusso, A. M.; Vitulli, G. J. Organomet. Chem.2000,607,57.
13. Saino, N.; Kogure, D.; Okamoto, S. Org. Lett.2005,7,3065.
14. (a) Bonnesen, P. V.; Puckett, C. L.; Honeychuck, R. V.; Hersh, W. H. J. Am. Chem. Soc.1989,111,6070. (b) Olson, A. S.; Seitz, W. J.; Hossain, M. M. Tetrahedron Lett.1991,32,5299. (c) Kelly, T. R.; Maity, S. K.; Meghani, P.; Chandrakumar, N. S. Tetrahedron Lett.1989,30,1357.
15. Chavan, S. P.; Sharma, A. K. Synlett.2001,667.
16. (a) Corey, E. J.; Ishihara, K. Tetrahedron Lett.1992,33,6807. (b) Corey, E. J.; Imai, N.; Zhang, H. Y. J. Am. Chem. Soc.1991,113,728. (c) Khiar, N.; Ferna'ndez, I.; Alcudia, F. Tetrahedron Lett.1993,34,123. (d) Matsukawa, S.; Sugama, H.; Imamoto, T. Tetrahedron Lett.2000,41,6461. (e) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E. J. Org. Chem.1997,62, 6454. (f) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto H., Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc.1998,120,.3074.
17. (a) Genet, J. P.; Ficini, J. Tetrahedron Lett.1979,1499. (b) Dieck, H. t.; Diercks, R. Angew. Chem., Int. Ed. Engl.1983,22,778. (c) Carbonaro, A.; Greco, A.; DallAsta, G. J. Org. Chem.1968,33,3948. (d) Carbonaro, A.; Greco, A.; DallAsta, G. J. Organomet. Chem.1969,20,111.
18. Genet, J. P.; Ficini, J. Tetrahedron Lett.1979,1499.
19. Carballo, R. M.; Ramirez, M. A.; Rodriguez, M. L.; Martin, V. S.; Padron, J. I. Org. Lett.2006,8,3837.
20. Miranda, P. O.; Carballo, R. M.; Martin, V. S.; Padron, J. I. Org. Lett.2009,11, 357.
21.Cao, K.; Zhang, F. M.; Tu, Y. Q.; Zhuo, X. T.; Fan, C. A. Chem. Eur. J.2009,15, 6332.
22. Shahzad, S. A.; Vivant, C.; Wirth, T. Org. Lett.2010,12,1364.
23. Correa, A.; Elmore, S.; Bolm, C. Angew. Chem. Int. Ed.2008,14,3527.
24. Correa, A.; Bolm, C.Adv. Synth. Catal.2008,350,391.
25. Correa, A,; Bolm, C. Angew. Chem. Int. Ed.2007,46,8862.
26. Correa A.; Carril M.; Bolm C. Angew. Chem. Int. Ed.2008,47,2880.
27. Guo, D.; Huang, H.; Xu, J.; Jiang, H.; Liu, H. Org. Lett.2008,10,4513.
28. Bistri, O.; Correa, A.; Bolm, C. Angew. Chem. Int. Ed.2008,47,586.
29. Nakanishi, M.; Salit, A.; Bolm, C. Adv. Synth. Catal.2008,350,1835.
30. (a) Redlich, M. D.; Mayer, M. F.; Hossain, M. M. Aldrichim. Acta 2003,36,3. (d) Seitz, W. J.; Hossain, M. M. Tetrahedron Lett.1994,35,7561. (b) Mahmood, S. J.; Saha, A. K.; Hossain, M. M. Tetrahedron 1998,54,349.
31. Legros, J.; Bolm, C. Chem. Eur. J.2005,11,1086.
32. Komeyama, K.; Morimoto, T.; Takaki, K. Angew. Chem. Int. Ed.2006,45,2938.
33. Terrason, V.; Michaux, J.; Gaucher, A.; Wehbe, J.; Marque, S.; Prim, D.; Campagne, J.-M. Eur. J. Org. Chem.2007,5332.
34. Carballo, R. M.; Ramirez, M. A.; Rodriguez, M. L.; Martin, V. S.; Padron, J. I. Org. Lett.2006,8,3837.
35. Bonnamour, J.; Bolm, C. Org. Lett.2008,10,2665.
36. Qiu, J. W.; Zhang, X. G.; Tang, R. Y.; Zhong, P.; Li, J. H. Adv. Synth. Catal.2009, 351,2319.
37. Guo, X.; Yu, R.; Li, H.; Li, Z. J. Am. Chem. Soc.2009,131,17387.
38. Gorman, D. B.; Tomlinson, I. A. Chem. Commun.1998,25.
39. For reviews, see:(a) Ma, D.; Cai, Q. Ace. Chem. Res.2008,41,1450. (b) Stanley, L. M.; Sibi, M. P. Chem. Rev.2008,108,2887. (c) Nakamura, I.; Yamamoto, Y. Chem. Rev.2004,104,2127. (d) Patil, N. T.; Yamamoto, Y. Chem. Rev.2008, 108,3395.
40. Liu, R.; Herron, S. R.; Fleming, S. A. J. Org. Chem.2007,72,5587.
41. Xu, Q.; Appella, D. H. Org. Lett.2008,10,1497.
42. Kinugasa, M.; Hashimoto, S. J. Chem. Soc. Chem. Commun.1972,466.
43. Lo, M. M. C.; Fu, G. C. J. Am. Chem. Soc.2002,124,4572-4573.
44. (a) Shintani, R.; Lo, M. M. C.; Fu, G. C. Org. Lett.2000,2,3695. (b) Shintani, R.; Fu, G. C. Org. Lett.2002,4,3699.
45. Shintani, R.; Fu, G. C. Angew. Chem., Int. Ed.2003,42,4082.
46. Lu, H.; Li, C. Org. Lett.2006,8,5365.
47. Lu, B. Wang, B. Zhang, Y.; Ma, D. J. Org. Chem.2007,72,5337.
48. Bates, C. G. Saejueng, P.; Murphy, J. M. Venkataraman, D. Org. Lett.2002,4, 4727.
49. Chen, Y.; Xie, X.; Ma, D. J. Org. Chem.2007,72,9329.
50. Chen, Y.; Wang, Y.; Sun, Z.; Ma, D. Org. Lett.2008,10,625.
51. Lu, B.; Ma, D. Org. Lett.2006,8,6115.
52. (a) Castro, C. E.; Stephens, R. D. J. Org. Chem.1963,28,2163. (b) Stephens, R. D.; Castro, C. E. J. Org. Chem.1963,28,3313.
53. Liu, F.; Ma,D. J. Org. Chem.2007,72,4844.
54. Li, L. Wang, M. Zhang, X. Jiang, Y. Ma, D. Org. Lett.2009,11,1309.
55. (a) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc.2001,123, 2074. (b) Kim, J. T.; Gevorgyan, V. Org. Lett.2002,4,4697.
56. Zou, B.; Yuan, Q.; Ma, D. Angew. Chem., Int. Ed.2007,46,2598.
57. Zou, B.; Yuan, Q.; Ma, D. Org. Lett.2007,9,4291.
58. Diao, X. Wang, Y. Jiang, Y. Ma, D. J. Org. Chem.2009,74,7974.
59. Zheng, N. Buchwald, S. L. Org. Lett.2007,9,4749.
60. Wang, B. Lu, B. Jiang, Y. Zhang, Y. Ma, D. Org. Lett.2008,10,2761.
61. Yuan, Q. Ma, D. J. Org. Chem.2008,73,5159.
62. Jones, C. P. Anderson, K. W. Buchwald, S. L. J. Org. Chem.2007,72,7968.
63. (a) Roesch, K. R.; Larock, R. C. Org. Lett.1999,1,553. (b) Roesch, K. R. Larock, R. C. J. Org. Chem.2002,67,86.
64. Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc.2000,122,1635.
65. Klapars, A. Parris, S. Anderson, K. W. Buchwald, S. L. J. Am. Chem. Soc.2004 126,3529.
66. Roberts, E. Sanction, J. P. Sweeney, J. B. Org. Lett.2005,7,2075.
67. Tang, T. Lin, C. Fu, H. Jiang, Y. Zhao, Y. Org. Lett.2005,7,4781.
68. (a) Ishizaki T.; Hashimoto Y.; Shudo K.; Okamato T.; Tetrahedron Lett.1982,23, (39),4055. (b) Ozden S.; Ozturk A. M.; Goker H.; Altanlar N. Ⅱ Farmaco 2000, 55,715.
69. Matsuoka, H.; Ohi, N.; Mihara, M.; Suzuki, H.; Miyamoto, K.; Maruyama, N.; Tsuji, K.; Kato, N.; Akimoto, T.; Takeda, Y.; Yano, K.; Kuroki, T, J. Med. Chem. 1997,40,105.
70. (a) La, D. S.; Belzile, J.; Bready, J. V.; Coxon, A.; DeMelfi, T.; Doerr, N.; Estrada, J.; Flynn, J. C.; Flynn, S. R.; Graceffa, R. F.; Harriman, S. P.; Larrow, J. F.; Long, A. M.; Martin, M. W.; Morrison, M. J.; Patel, V. F.; Roveto, P. M.; Wang, L.; Weiss, M. M.; Whittington, D. A.; Teffera, Y.; Zhao, Z. Polverino, A. J.; Harmange, J. J. Med. Chem.2008,51,1695.
71. (a) Fringuelli R.; Giacche N.; Milanese L.; Cenci E.; Macchiarulo A.; Vecchiarelli A.; Costantino G.; Schiaffella F. Bioorg. Med. Chem.2009,17,3838. (b) Fringuelli R.; Pietrella D.; Schiaffella F.; Guarraci A.; Perito S.; Bistonib F.; Vecchiarellib A. Bioorg. Med. Chem.2002,10,1681.
72. (a) Wahlroos O.; Virtanen A. I.; Acta. Chem. Scand.1959,13,1906; (b) Virtanen A. I.; Hietala P. K.; Acta. Chem. Scand.1960,14,(2),499; (c) Hietala P. K.; Virtanen A. I.; Acta. Chem. Scand.1960,14, (2),502; (d) Tipton C. L.; Klun J. A.; Husted R. R.; Pierson M. D. Biochemistry 1967,6,2866; (e) Klun J. A.; Tipton C. L.; Robinson J. F.; Ostreem D. L.; Beroza M.; Agric. Food. Chem.1970,18, (4), 663; (f) Tipton C. L.; Wang M. C.; Tasao F. H.; Lintu C. C.; Husted R. R. Phytochemistry 1973,12, (3),347.
73. (a) Hayakawa, I.; Atarashi, S.; Yokohama, S.; Imamura, M.;Sakano, K.; Furukawa, M. Antimicrob. Agents Chemother.1986,29,163. (b) Atar ashi, S.; Yokohama, S.; Yamazaki, U.; Sakano, K.; Imamura, M.; Hayakawa, I. Chem. Pharm. Bull.1987, 35,1896. (c) Mitscher, L. A.; Gharma, P. N.; Chu, D. T. W.; Shen, L. L.; Pernet, A. G J. Med. Chem.1987,30,2283. (d) Atarashi, S.; Tsurumi, H.; Fujiwara, T.; Hayakawa, I. J. Heterocycl. Chem.1991,28,329. (e) Kosemura, S.; Yamamura, S.; Anai, T.; Hasegawa, K. Tetrahedron Lett.1994,35,8221. (f) Nishio, T.; Omote, Y. J. Org. Chem.1985,50,1370. (g) Marubayashi, N.; Ogawa, T.; Kuroita, T.; Hamasaki, T.; Ueda, I. Tetrahedron Lett.1992,33,4585.
74. (a) Buon C.; Lefevre L. C.; Rabot R.; Bouyssou P.; Coudert G Tetrahedron 2000, 56,605. (b) Mizar P.; Myrboh B. Tetrahedron Lett.2006,47,7823. (c) Bourlot A. S.; Sanchez I.; Dureng G.; Guillaumet G.; Massingham R.; Monteil A.; Winslow E.; Pujol M. D.; Merour J. Y. J. Med. Chem.1998,41,3142.
75. Bunce R. A.; Herron D. M. Hale L. Y. J. Heterocyclic Chem.2003,40,1031.
76. Kundu N. G.; Chaudhuri G.; Upadhyay A. J. Org. Chem.2001,66,20.
77. (a) Yamamoto, Y.; Hayashi, H.; Saigoku, T.; Nishiyama, H. J. Am. Chem. Soc. 2005,127,10804; (b) Balme, G Angew. Chem., Int. Ed.2004,43,6238; (c) Tejedor, d.; Gonzalez-Cruz, D.; Garcia-Tellado, F.; Marrero-Tellado, J. J.; Rodriguez, M. L. J. Am. Chem. Soc.2004,126,8390; (d) Dhawan, R.; Arndtsen, B. A. J. Am. Chem. Soc.2004,126,468.
78. (a) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed.2003,42,5763; (b) Dyatkin, A. B.; Rivero, R. A. Tetrahedron Lett.1998,39, 3647; (c) Bieber, L. W.; da Silva, M. F. Tetrahedron Lett.2004,45,8281.
79. Wei, C.; Li, Z.; Li, C. J. Org. Lett.2003,5,4473.
80. (a) Wei, C.; Li, C. J. J. Am. Chem. Soc.2003,125,9584; (b) Lo, V. K.-Y.; Liu, Y.; Wong, M.-K.; Che, C. M. Org. Lett.2006,8,1529; (c) Xiao, F.; Chen, Y.; Liu, Y.; Wang, J. Tetrahedron Lett.2008,64,2755.
81. Li, C. J.; Wei, C. Chem. Commun.2002,268.
82. Fischer, C.; Carreira, E. M. Org. Lett.2001,3,4319.
83. Park, S. B.; Alper, H. Chem. Commun.2005,1315.
84. Choudary, B. M.; Sridhar, C.; Kantam, M. L.; Sreedhar, B. Tetrahedron Lett.2004, 45,7319.
85. Shi, L.; Tu, Y Q.; Wang, M.; Zhang, F. M.; Fan, C. A. Org. Lett.2004,6,1001.
86. Sreedhar, B.; Reddy, S.; Prakash, B. V.; Ravindra, A. Tetrahedron Lett.2005,46, 7019.
87. Shi, L.; Tu, Y.; Wang, M.; Zhang, F.; Fan, C. Org. Lett.2004,6,1001.
88. (a) Jager, V.; Gunther, H. J. Tetrahedron Lett.1977,2543. (b) Yamamoto, M. J. Chem. Soc., Chem. Commun.1978,649. (c) Arcadi, A.; Burini, A.; Cacchi, S.; Delmastro, M.; Marinelli, F.; Pictroni, B. R. J. Org. Chem.1992,57,976.
89. For selected examples, see:(a) S. Seo, X. Yu, T. J. Marks, J. Am. Chem. Soc.2009, 131,263. (b) A. Dzudza, T. J. Marks, Org. Lett.2009,11,1523. (c) X. Yu, S. Seo, T. J. Marks, J. Am. Chem. Soc.2007,129,7244. (d) J. Barluenga, A. Fernandez, A. Satrustegui, A. Dieguez, F. Rodriguez, J. Fananas, Chem. Eur. J.2008,14,4153. (e) L. A. Adrio, K. K. Hii, Chem. Commun.2008,2325. (f) L. Coulombel, M. Rajzmann, J. M. Pons, S. Olivero, E. Dunach, Chem. Eur. J.2006,12,6356. (g) C.-G. Yang, C. He, J. Am. Chem. Soc.2005,127,6966. (h) Y. Oe, T. Ohta, Y. Ito, Synlett.2005,1,179. (i) H. Qian, X. Han, R. A. Widenhoefer, J. Am. Chem. Soc. 2004,126,9536. (j) K. Komeyama, T. Morimoto, Y. Nakayama, K. Takaki, Tetrahedron Lett.2007,48,3259. (k) C.-G. Yang, N. W. Reich, Z. Shi, Org. Lett. 2005,7,4553. (1) D. C. Rosenfeld, S. Shekhar, A. Takemiya, M. Utsunomiya, J. F. Hartwig, Org. Lett.2006,8,4179. (m) R. V. Nguyen, X. Q. Yao, C. J. Li, Org. Lett. 2006,8,2397. (n) S. W. Youn, J. I. Eom, J. Org. Chem.2006,71,6705. (o) L. Coulombel, I. Favier, E. Dunach, Chem. Commun.2005,2286. (p) Y. Nishibayashi, Y. Inada, M. Yoshikawa, M. Hidai, S. Uemura, Angew. Chem. Int. Ed.2003,42,1495. (q) F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev.2004,104, 3079, and references cited therein. (r) Y. Liu, F. Song, Z. Song, M. Liu, B. Yan, Org. Lett.2005,7,5409.
90. Komeyama K.; Morimoto T.; Nakayama Y; Takaki K. Tetrahedron Lett.2007,48, 3259.
91. Komeyama K.; Mieno Y.; Yukawa S.; Morimoto T.; Takaki K. Chem. Lett.2007, 36,752.
92. Baldwin, J. E. J. Chem. Soc. Chem. Commun.1976,734.
93. Liu, Z.; Liu, L.; Shafiq, Z.; Wu, Y.; Wang, D.; Chen, Y. Synthesis 2007,13,1961.
94. Nishibayashi, Y.; Inada, Y.; Yoshikawa, M.; Hidai, M.; Uemura, S. Angew. Chem. Int. Ed.2003,42,1495.
95. Sanz R.; Martinez A.; Alvarez-Gutierrez J. M.; Rodriguez F. Eur. J. Org. Chem. 2006,1383.
96. Liu J.; Muth E.; Florke U.; Henkel G.; Merz K.; Sauvageau J.; Schwake E.; Dyker G. Adv. Synth. Catal.2006,348,456.
97. Srihari P.; Bhunia D. C.; Sreedhar P.; Mandal S. S.; Reddy J. S. S.; Yadav J. S. Tetrahedron Lett.2007,48,8120.
98. Nishibayashi Y.; Inada Y.; Yoshikawa M.; Hidai M.; Uemura S. Angew. Chem. Int. Ed.2003,42,1495.
99. (a) Zhan Z. P.; Cui Y. Y.; Liu H. J. Tetrahedron Lett.2006,47,9143; (b) Zhan Z. P.; Yu J. L.; Liu H. J.; Cui Y Y.; Yang R. F.; Yang W. Z.; Li J. P. J. Org. Chem.2006, 71,8298.
100. Zhan Z. P.; Yang W. Z.; Yang R. F.; Yu J. L.; Li J. P.; Liu H. J. Chem. Commun. 2006,3352.
101. Georgy M.; Boucard V.; Campagne J. M. J. Am. Chem. Soc.2005,127,14180.
102. Karunakar G. V.; Periasamy M. J. Org. Chem.2006,71,7463.
103. Kennedy-Smith J. J.; Young L. A.; Toste F. D. Org. Lett.2004,6,1325.
104. Dyker, G Handbook of C-H Transformations; Wiley-VCH: Weinheim,2005.
105. (a) Roesky, P. W. Angew. Chem., Int. Ed.2009,48,2. (b) Li, C. J. Acc. Chem. Res.2009,42,335. (c) Bergman, R. G. Nature 2007,446,391. (d) Campos, K. R. Chem. Soc. Rev.2007,36,1069. (e) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007,36,1173. (f) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev.2007,107, 174. (g) Godula, K.; Sames, D. Science 2006,312,67. (h) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev.2002,102,1731. (i) Dyker, G. Angew. Chem., Int. Ed. 1999,38,1698. (j) Shilov, A. E.; Shul'pin, G. B. Chem. Rev.1997,97,2879.
106. Norinder, J.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. J. Am. Chem. Chem. 2008,130,5858.
107. (a) Vallee, F.; Mousseau, J. J.; Charette, A. J. Am. Chem. Chem.2010,132,1514. (b) Liu, W.; Cao, H.; Lei, A. Angew. Chem. Int. Ed.2010,49,1.
108. Iovel, I.; Mertins, K.; Kischel, J.; Zapf, A.; Beller, M. Angew. Chem. Int. Ed. 2005,44,3913.
109. Li, Y. Z.; Li, B. J.; Lu, X. Y.; Lin, S.; Shi, Z. J. Angew. Chem. Int. Ed.2009,48, 3817.
110. (a) Li, Z.; Yu, R.; Li, H. Angew. Chem. Int. Ed.2008,47,7497. (b) Li, H.; He, Z.; Guo, X.; Li, W.; Zhao, X.; Li, Z. Org. Lett.2009,11, 4176.
111. (a) Peters AT, Freeman HS. Color chemistry: the design and synthesis of organic dyes and pigments. Barking, Essex:Appl Sci Publ Ltd; 1991. p193. (b) Gregory P. High-technology applications of organic colorants. New York and London: Plenum Press; 1991.p1.
112. Nolan, E. M.; Racine, M. E.; Lippard, S. J. Inorg. Chem.2006,45,2742.
113. Muniz, F. M.; Alcazar, V.; Simon, L.; Raposo, C.; Calle, E.; Moran, J. R. Eur. J. Org. Chem.2009,1009.
114. Hideu, T. Jpn. Tokkyo Koho JP,56005480; 1981 Chem. Abstr.1981,95,80922b. Lamberk RW, Martin JA, Merrett JH, Parkes KEB, Thomas GJ. PCT Int. Appl.
115. WO 9706178; 1997 Chem. Abstr.1997,126, P212377y.
116. Poupelin, J. P.; Saint-Rut, G.; Fussard-Blanpin, O.; Narcisse, G.; Uchida-Ernouf, G.; Lakroix, R. Eur. J. Med. Chem.1978,13,67.
117. Kraim, K.; Khatmi, D.; Saihi, Y.; Ferkous, F.; Brahimi, M. Chemom. Intel. Lab. Sys.2009,97,118.
118. Khosropour, A. R.; Khodaei, M. M.; Moghannian, H. Synlett.2005,955.
119. Rajitha, B.; Kumar, B. S.; Reddy, Y. T.; Reddy, P.; Sreenivasulu, N. Tetrahedron Lett.2005,46,8691.
120. Sarma, R. J.; Baruah, J. B. Dyes Pigments 2005,64,91.
121. Das, B.; Ravikanth, B.; Ramu, R.; Laxminarayana, K.; Rao, B. V. J. Mol. Catal. A:Chem.2006,255,74.
122. Pasha, M. A.; Jayashankara, V. P. Bioorg. Med. Chem. Lett.2007,17,621.
123. Nagarapu, L.; Kantevari, S.; Mahankhali, V. C.; Apuri, S. Catal. Commun.2007, 8,1173.
124. Bigdeli, M. A.; Heravi, M. M.; Mahdavinia, G. H. Catal. Commun.2007,8, 1595.
125. Saini, A.; Kumar, S.; Sandhu, J. S. Synlett.2006,1928.
126. Su W. K.; Yang D.; Jin C.; Zhang B. Tetrahedron Lett.2008,49,3391.
127. Singh, R.; Panda, G. Org. Biomol. Chem.2010,8,1097.
128. Li, H.; Yang, J.; Liu, Y. Li, Y. J. Org. Chem.2009,74,6797.
129. Yoshida H.; Watanabe M.; Fukushima H.; Ohshita J.; Kunai A. Org. Lett.2004,6, 4049.
130. Okuma, K.; Nojima, A.; Matsunaga, N.; Shioji, K. Org. Lett.2009,11,169.
131. Angeli, A. Gazz. Chim. Ital.1890,26,1793.
132. Scholtz, M. Ber. Dtsch. Chem. Ges.1912,45,734.
133. For recent reviews, see:(a) Micheal, J. P. Alkaloids 2001,55,91. (b) Micheal, J. P. Nat. Prod. Rep.2002,19,742.
134. Jorgensen, A. S.; Jacobsen, P.; Christiansen, L. B.; Bury, P. S.; Kanstrup, A.; Thorpe, S. M.; Naerum, L.; Wassermann, K. Bio. Med. Chem. Lett.2000,10, 2383.
135. Bermudez, J.; Fake, C. S.; Joiner, G F.; King, F. D.; Miner, W. D.; Sanger, G J. J. Med. Chem.1990,33,1924.
136. Gubin, J.; Lucchetti, J.; Mahaux, J.; Nisato, D.; Rosseels, G.; Clinet, M.; Polster, P.; Chatelain, P. J. J. Med. Chem.1992,35,981.
137. (a) Nash, R. J.; Fellows, L. E.; Dring, J. V.; Striton, C. H.; Carter,D.; Hegarty, M. P.; Bell, E. A. Phytochemistry 1988,27,1403. (b)Molyneux, R. J.; James, L. F. Science 1982,216,190.
138. Taguchi, T. U. S. Patent 0015614-A1,2001.
139. Wani, M. C; Bonman, P. E.; Lindley, J. T.; Wall, M. E. J. Med. Chem.1980,23, 554.
140.吴达,梁冰,冯志刚,师彦平。中兽医医药杂志,2003,42.
141. Chichibabin, A. E. Chem. Ber.1927,60,1607.
142. Borrows, E. T.; Holland, D. O.; Kenyon, J. J. Chem. Soc.1946,1069.
143. Bragg, D. R.; Wibberly, D. G. J. Chem. Soc.1963,3277.
144. Henrick, C. A.; Ritchie, E.; Taylor, W. C. Aust. J. Chem.1967,20,2467.
145. Wei, J.; Hu, Y.; Li, T.; Hu, H. J. Chem. Soc. Perkin trans.11993,2487.
146. Hou, J.; Hu, Y; Hu, H. Synth. Commun.199.8,28,3397.
147. Matsumoto, K.; Ogasawara, A.; Kimura, S.; Hayashi, N.; Machiguchi, T. Heterocycles 1998,48,861.
148. Kel'in A. V.; Sromek A. W.; Gevorgyan V. J. Am. Chem. Soc.2001,123,2074.
149. Kim J. T.; Butt J.; Gevorgyan V. J. Org. Chem.2004,69,5638.
150. Chernyak D.; Gadamsetty S. B.; Gevorgyan V. Org. Lett.2008,10,2307.
151. Chuprakov S.; Hwang F. W.; Gevorgyan V. Angew. Chem. Int. Ed.2007,46, 4757.
152. Chuprakov S.; Gevorgyan V. Org. Lett.2007,9,4463.
153. Yan, B.; Zhou, Y.; Zhang, H.; Chen, J. Liu, Y. J. Org. Chem.2007,72,7783.
154. Yan, B.; Liu, Y. Org. Lett.2007,9,4323.
155. Liu, Y.; Song, Z.; Yan, B. Org. Lett.2007,9,409.
156. Glamkowski, E. J.; Fortunato, J. M.; Spaulding, T. C.; Wilker, J. C.; Ellis, D. B. J. Med. Chem.1985,28,66.
157. Unangst, P. C.; Carethers, M. E.; Webster, K.; Janik, G. M.; Robichaud, L. J. J. Med. Chem.1984,27,1629.
158. Kamat, A. G.; Gadaginamath, G S. Indian J. Chem.1994,33,255.
159. Perregaard, J.; Arnt, J.; Boegesoe, K. P.; Hyttel, J.; Sanchez, C. J. Med. Chem. 1992,35,1092.
160. Cole, D. C.; Ellingboe, J. W.; Lennox, W. J.; Mazandarani, H.; Smith, D. L.; Stock, J. R.; Zhang, G. M.; Zhou, P.; Schechter, L. E. Bioorg. Med. Chem. Lett. 2005,15,379.
161. Li, Q.; Li, T. M.; Woods, K. W.; Gu, W. Z.; Cohen, J.; Stoll, V. S.; Galicia, T.; Hutchins, C.; Frost, D.; Rosenberg, S. H.; Sham, H. L. Bioorg. Med. Chem. Lett. 2005,15,2918.
162. Xu, H.; Liu, W. Q.; Fan, L. L.; Chen, Y.; Yang, L. M.; Lv, L.; Zheng, Y. T. Chem. Pharm. Bull.2008,6,720.
163. (a) For review, see:Lindley, J. Tetrahedron 1984,40,1433. (b) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc.1998,120,12459. (c) Ma, D.; Xia, C. Org. Lett.2001,3,2583. (d) Weingarten, H. J. Org. Chem.1964,29,3624. (e) Shimakawa, R. O.; Takenaka, S. Chem. Lett.1988,899. (f) Marcoux, J. F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc.1997,119,10539. (g) Cristau, H.; Cellier, P. P.; Spindler, J.; Taillefer, M. Chem. Eur. J.2004,10,5607. (h) Grasa, G A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem.2001,66,7729.
164. Ackermann, L.; Barfuber, S.; Potukuchia, H. K. Adv. Synth. Catal.2009,351, 1064.
2. (a) Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jφrgensen, K. A., Eds.; Wiley-VCH:Weinheim,2002. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev.1996,96,635.
3. Lautens, M.; Klute, W.; Tam, W. Chem. Rev.1996,96,49.
4. Morandi, B.; Carreira, E. M. Angew. Chem. Int. Ed.2010,49,938.
5. (a) Hamaker, C. G.; Mirafzal, G. A.; Woo, L. K. Organometallics 2001,20,5171. (b) Edulji, S. K.; Nguyen, S. T. Organometallics 2003,22,3374.
6. Ohara, H.; Itoh, T.; Nakamura, M.; Nakamura, E. Chem. Lett.2001,624.
7. Rosenblum, M.; Scheck, D. Organometallics 1982,1,397.
8. Bouwkamp, M. W.; Bowman, A. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Chem.2006,128,13340.
9. Taniguchi, T.; Ishibashi, H. Org. Lett.2010,12,124.
10. Cantagrel, G.; de Carne Carnavalet, B.; Meyer, C.; Cossy, J. Org. Lett.2009,11, 4262.
11. (a) Breschi, C.; Piparo, L.; Pertici, P.; Caporusso, A. M.; Vitulli, G J. Organomet. Chem.2000,607,57. (b) Funhoff, A.; Schaufele, H.; Zenneck, U. J. Organomet. Chem.1988,345,331. (c) Usieli, V.; Victor, R.; Sarel, S. Tetrahedron Lett.1976, 2705. (d) Hubel, W.; Hoogzand, C. Chem. Ber.1960,93,103.
12. Breschi, C.; Piparo, L.; Pertici, P.; Caporusso, A. M.; Vitulli, G. J. Organomet. Chem.2000,607,57.
13. Saino, N.; Kogure, D.; Okamoto, S. Org. Lett.2005,7,3065.
14. (a) Bonnesen, P. V.; Puckett, C. L.; Honeychuck, R. V.; Hersh, W. H. J. Am. Chem. Soc.1989,111,6070. (b) Olson, A. S.; Seitz, W. J.; Hossain, M. M. Tetrahedron Lett.1991,32,5299. (c) Kelly, T. R.; Maity, S. K.; Meghani, P.; Chandrakumar, N. S. Tetrahedron Lett.1989,30,1357.
15. Chavan, S. P.; Sharma, A. K. Synlett.2001,667.
16. (a) Corey, E. J.; Ishihara, K. Tetrahedron Lett.1992,33,6807. (b) Corey, E. J.; Imai, N.; Zhang, H. Y. J. Am. Chem. Soc.1991,113,728. (c) Khiar, N.; Ferna'ndez, I.; Alcudia, F. Tetrahedron Lett.1993,34,123. (d) Matsukawa, S.; Sugama, H.; Imamoto, T. Tetrahedron Lett.2000,41,6461. (e) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E. J. Org. Chem.1997,62, 6454. (f) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto H., Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc.1998,120,.3074.
17. (a) Genet, J. P.; Ficini, J. Tetrahedron Lett.1979,1499. (b) Dieck, H. t.; Diercks, R. Angew. Chem., Int. Ed. Engl.1983,22,778. (c) Carbonaro, A.; Greco, A.; DallAsta, G. J. Org. Chem.1968,33,3948. (d) Carbonaro, A.; Greco, A.; DallAsta, G. J. Organomet. Chem.1969,20,111.
18. Genet, J. P.; Ficini, J. Tetrahedron Lett.1979,1499.
19. Carballo, R. M.; Ramirez, M. A.; Rodriguez, M. L.; Martin, V. S.; Padron, J. I. Org. Lett.2006,8,3837.
20. Miranda, P. O.; Carballo, R. M.; Martin, V. S.; Padron, J. I. Org. Lett.2009,11, 357.
21.Cao, K.; Zhang, F. M.; Tu, Y. Q.; Zhuo, X. T.; Fan, C. A. Chem. Eur. J.2009,15, 6332.
22. Shahzad, S. A.; Vivant, C.; Wirth, T. Org. Lett.2010,12,1364.
23. Correa, A.; Elmore, S.; Bolm, C. Angew. Chem. Int. Ed.2008,14,3527.
24. Correa, A.; Bolm, C.Adv. Synth. Catal.2008,350,391.
25. Correa, A,; Bolm, C. Angew. Chem. Int. Ed.2007,46,8862.
26. Correa A.; Carril M.; Bolm C. Angew. Chem. Int. Ed.2008,47,2880.
27. Guo, D.; Huang, H.; Xu, J.; Jiang, H.; Liu, H. Org. Lett.2008,10,4513.
28. Bistri, O.; Correa, A.; Bolm, C. Angew. Chem. Int. Ed.2008,47,586.
29. Nakanishi, M.; Salit, A.; Bolm, C. Adv. Synth. Catal.2008,350,1835.
30. (a) Redlich, M. D.; Mayer, M. F.; Hossain, M. M. Aldrichim. Acta 2003,36,3. (d) Seitz, W. J.; Hossain, M. M. Tetrahedron Lett.1994,35,7561. (b) Mahmood, S. J.; Saha, A. K.; Hossain, M. M. Tetrahedron 1998,54,349.
31. Legros, J.; Bolm, C. Chem. Eur. J.2005,11,1086.
32. Komeyama, K.; Morimoto, T.; Takaki, K. Angew. Chem. Int. Ed.2006,45,2938.
33. Terrason, V.; Michaux, J.; Gaucher, A.; Wehbe, J.; Marque, S.; Prim, D.; Campagne, J.-M. Eur. J. Org. Chem.2007,5332.
34. Carballo, R. M.; Ramirez, M. A.; Rodriguez, M. L.; Martin, V. S.; Padron, J. I. Org. Lett.2006,8,3837.
35. Bonnamour, J.; Bolm, C. Org. Lett.2008,10,2665.
36. Qiu, J. W.; Zhang, X. G.; Tang, R. Y.; Zhong, P.; Li, J. H. Adv. Synth. Catal.2009, 351,2319.
37. Guo, X.; Yu, R.; Li, H.; Li, Z. J. Am. Chem. Soc.2009,131,17387.
38. Gorman, D. B.; Tomlinson, I. A. Chem. Commun.1998,25.
39. For reviews, see:(a) Ma, D.; Cai, Q. Ace. Chem. Res.2008,41,1450. (b) Stanley, L. M.; Sibi, M. P. Chem. Rev.2008,108,2887. (c) Nakamura, I.; Yamamoto, Y. Chem. Rev.2004,104,2127. (d) Patil, N. T.; Yamamoto, Y. Chem. Rev.2008, 108,3395.
40. Liu, R.; Herron, S. R.; Fleming, S. A. J. Org. Chem.2007,72,5587.
41. Xu, Q.; Appella, D. H. Org. Lett.2008,10,1497.
42. Kinugasa, M.; Hashimoto, S. J. Chem. Soc. Chem. Commun.1972,466.
43. Lo, M. M. C.; Fu, G. C. J. Am. Chem. Soc.2002,124,4572-4573.
44. (a) Shintani, R.; Lo, M. M. C.; Fu, G. C. Org. Lett.2000,2,3695. (b) Shintani, R.; Fu, G. C. Org. Lett.2002,4,3699.
45. Shintani, R.; Fu, G. C. Angew. Chem., Int. Ed.2003,42,4082.
46. Lu, H.; Li, C. Org. Lett.2006,8,5365.
47. Lu, B. Wang, B. Zhang, Y.; Ma, D. J. Org. Chem.2007,72,5337.
48. Bates, C. G. Saejueng, P.; Murphy, J. M. Venkataraman, D. Org. Lett.2002,4, 4727.
49. Chen, Y.; Xie, X.; Ma, D. J. Org. Chem.2007,72,9329.
50. Chen, Y.; Wang, Y.; Sun, Z.; Ma, D. Org. Lett.2008,10,625.
51. Lu, B.; Ma, D. Org. Lett.2006,8,6115.
52. (a) Castro, C. E.; Stephens, R. D. J. Org. Chem.1963,28,2163. (b) Stephens, R. D.; Castro, C. E. J. Org. Chem.1963,28,3313.
53. Liu, F.; Ma,D. J. Org. Chem.2007,72,4844.
54. Li, L. Wang, M. Zhang, X. Jiang, Y. Ma, D. Org. Lett.2009,11,1309.
55. (a) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc.2001,123, 2074. (b) Kim, J. T.; Gevorgyan, V. Org. Lett.2002,4,4697.
56. Zou, B.; Yuan, Q.; Ma, D. Angew. Chem., Int. Ed.2007,46,2598.
57. Zou, B.; Yuan, Q.; Ma, D. Org. Lett.2007,9,4291.
58. Diao, X. Wang, Y. Jiang, Y. Ma, D. J. Org. Chem.2009,74,7974.
59. Zheng, N. Buchwald, S. L. Org. Lett.2007,9,4749.
60. Wang, B. Lu, B. Jiang, Y. Zhang, Y. Ma, D. Org. Lett.2008,10,2761.
61. Yuan, Q. Ma, D. J. Org. Chem.2008,73,5159.
62. Jones, C. P. Anderson, K. W. Buchwald, S. L. J. Org. Chem.2007,72,7968.
63. (a) Roesch, K. R.; Larock, R. C. Org. Lett.1999,1,553. (b) Roesch, K. R. Larock, R. C. J. Org. Chem.2002,67,86.
64. Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc.2000,122,1635.
65. Klapars, A. Parris, S. Anderson, K. W. Buchwald, S. L. J. Am. Chem. Soc.2004 126,3529.
66. Roberts, E. Sanction, J. P. Sweeney, J. B. Org. Lett.2005,7,2075.
67. Tang, T. Lin, C. Fu, H. Jiang, Y. Zhao, Y. Org. Lett.2005,7,4781.
68. (a) Ishizaki T.; Hashimoto Y.; Shudo K.; Okamato T.; Tetrahedron Lett.1982,23, (39),4055. (b) Ozden S.; Ozturk A. M.; Goker H.; Altanlar N. Ⅱ Farmaco 2000, 55,715.
69. Matsuoka, H.; Ohi, N.; Mihara, M.; Suzuki, H.; Miyamoto, K.; Maruyama, N.; Tsuji, K.; Kato, N.; Akimoto, T.; Takeda, Y.; Yano, K.; Kuroki, T, J. Med. Chem. 1997,40,105.
70. (a) La, D. S.; Belzile, J.; Bready, J. V.; Coxon, A.; DeMelfi, T.; Doerr, N.; Estrada, J.; Flynn, J. C.; Flynn, S. R.; Graceffa, R. F.; Harriman, S. P.; Larrow, J. F.; Long, A. M.; Martin, M. W.; Morrison, M. J.; Patel, V. F.; Roveto, P. M.; Wang, L.; Weiss, M. M.; Whittington, D. A.; Teffera, Y.; Zhao, Z. Polverino, A. J.; Harmange, J. J. Med. Chem.2008,51,1695.
71. (a) Fringuelli R.; Giacche N.; Milanese L.; Cenci E.; Macchiarulo A.; Vecchiarelli A.; Costantino G.; Schiaffella F. Bioorg. Med. Chem.2009,17,3838. (b) Fringuelli R.; Pietrella D.; Schiaffella F.; Guarraci A.; Perito S.; Bistonib F.; Vecchiarellib A. Bioorg. Med. Chem.2002,10,1681.
72. (a) Wahlroos O.; Virtanen A. I.; Acta. Chem. Scand.1959,13,1906; (b) Virtanen A. I.; Hietala P. K.; Acta. Chem. Scand.1960,14,(2),499; (c) Hietala P. K.; Virtanen A. I.; Acta. Chem. Scand.1960,14, (2),502; (d) Tipton C. L.; Klun J. A.; Husted R. R.; Pierson M. D. Biochemistry 1967,6,2866; (e) Klun J. A.; Tipton C. L.; Robinson J. F.; Ostreem D. L.; Beroza M.; Agric. Food. Chem.1970,18, (4), 663; (f) Tipton C. L.; Wang M. C.; Tasao F. H.; Lintu C. C.; Husted R. R. Phytochemistry 1973,12, (3),347.
73. (a) Hayakawa, I.; Atarashi, S.; Yokohama, S.; Imamura, M.;Sakano, K.; Furukawa, M. Antimicrob. Agents Chemother.1986,29,163. (b) Atar ashi, S.; Yokohama, S.; Yamazaki, U.; Sakano, K.; Imamura, M.; Hayakawa, I. Chem. Pharm. Bull.1987, 35,1896. (c) Mitscher, L. A.; Gharma, P. N.; Chu, D. T. W.; Shen, L. L.; Pernet, A. G J. Med. Chem.1987,30,2283. (d) Atarashi, S.; Tsurumi, H.; Fujiwara, T.; Hayakawa, I. J. Heterocycl. Chem.1991,28,329. (e) Kosemura, S.; Yamamura, S.; Anai, T.; Hasegawa, K. Tetrahedron Lett.1994,35,8221. (f) Nishio, T.; Omote, Y. J. Org. Chem.1985,50,1370. (g) Marubayashi, N.; Ogawa, T.; Kuroita, T.; Hamasaki, T.; Ueda, I. Tetrahedron Lett.1992,33,4585.
74. (a) Buon C.; Lefevre L. C.; Rabot R.; Bouyssou P.; Coudert G Tetrahedron 2000, 56,605. (b) Mizar P.; Myrboh B. Tetrahedron Lett.2006,47,7823. (c) Bourlot A. S.; Sanchez I.; Dureng G.; Guillaumet G.; Massingham R.; Monteil A.; Winslow E.; Pujol M. D.; Merour J. Y. J. Med. Chem.1998,41,3142.
75. Bunce R. A.; Herron D. M. Hale L. Y. J. Heterocyclic Chem.2003,40,1031.
76. Kundu N. G.; Chaudhuri G.; Upadhyay A. J. Org. Chem.2001,66,20.
77. (a) Yamamoto, Y.; Hayashi, H.; Saigoku, T.; Nishiyama, H. J. Am. Chem. Soc. 2005,127,10804; (b) Balme, G Angew. Chem., Int. Ed.2004,43,6238; (c) Tejedor, d.; Gonzalez-Cruz, D.; Garcia-Tellado, F.; Marrero-Tellado, J. J.; Rodriguez, M. L. J. Am. Chem. Soc.2004,126,8390; (d) Dhawan, R.; Arndtsen, B. A. J. Am. Chem. Soc.2004,126,468.
78. (a) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed.2003,42,5763; (b) Dyatkin, A. B.; Rivero, R. A. Tetrahedron Lett.1998,39, 3647; (c) Bieber, L. W.; da Silva, M. F. Tetrahedron Lett.2004,45,8281.
79. Wei, C.; Li, Z.; Li, C. J. Org. Lett.2003,5,4473.
80. (a) Wei, C.; Li, C. J. J. Am. Chem. Soc.2003,125,9584; (b) Lo, V. K.-Y.; Liu, Y.; Wong, M.-K.; Che, C. M. Org. Lett.2006,8,1529; (c) Xiao, F.; Chen, Y.; Liu, Y.; Wang, J. Tetrahedron Lett.2008,64,2755.
81. Li, C. J.; Wei, C. Chem. Commun.2002,268.
82. Fischer, C.; Carreira, E. M. Org. Lett.2001,3,4319.
83. Park, S. B.; Alper, H. Chem. Commun.2005,1315.
84. Choudary, B. M.; Sridhar, C.; Kantam, M. L.; Sreedhar, B. Tetrahedron Lett.2004, 45,7319.
85. Shi, L.; Tu, Y Q.; Wang, M.; Zhang, F. M.; Fan, C. A. Org. Lett.2004,6,1001.
86. Sreedhar, B.; Reddy, S.; Prakash, B. V.; Ravindra, A. Tetrahedron Lett.2005,46, 7019.
87. Shi, L.; Tu, Y.; Wang, M.; Zhang, F.; Fan, C. Org. Lett.2004,6,1001.
88. (a) Jager, V.; Gunther, H. J. Tetrahedron Lett.1977,2543. (b) Yamamoto, M. J. Chem. Soc., Chem. Commun.1978,649. (c) Arcadi, A.; Burini, A.; Cacchi, S.; Delmastro, M.; Marinelli, F.; Pictroni, B. R. J. Org. Chem.1992,57,976.
89. For selected examples, see:(a) S. Seo, X. Yu, T. J. Marks, J. Am. Chem. Soc.2009, 131,263. (b) A. Dzudza, T. J. Marks, Org. Lett.2009,11,1523. (c) X. Yu, S. Seo, T. J. Marks, J. Am. Chem. Soc.2007,129,7244. (d) J. Barluenga, A. Fernandez, A. Satrustegui, A. Dieguez, F. Rodriguez, J. Fananas, Chem. Eur. J.2008,14,4153. (e) L. A. Adrio, K. K. Hii, Chem. Commun.2008,2325. (f) L. Coulombel, M. Rajzmann, J. M. Pons, S. Olivero, E. Dunach, Chem. Eur. J.2006,12,6356. (g) C.-G. Yang, C. He, J. Am. Chem. Soc.2005,127,6966. (h) Y. Oe, T. Ohta, Y. Ito, Synlett.2005,1,179. (i) H. Qian, X. Han, R. A. Widenhoefer, J. Am. Chem. Soc. 2004,126,9536. (j) K. Komeyama, T. Morimoto, Y. Nakayama, K. Takaki, Tetrahedron Lett.2007,48,3259. (k) C.-G. Yang, N. W. Reich, Z. Shi, Org. Lett. 2005,7,4553. (1) D. C. Rosenfeld, S. Shekhar, A. Takemiya, M. Utsunomiya, J. F. Hartwig, Org. Lett.2006,8,4179. (m) R. V. Nguyen, X. Q. Yao, C. J. Li, Org. Lett. 2006,8,2397. (n) S. W. Youn, J. I. Eom, J. Org. Chem.2006,71,6705. (o) L. Coulombel, I. Favier, E. Dunach, Chem. Commun.2005,2286. (p) Y. Nishibayashi, Y. Inada, M. Yoshikawa, M. Hidai, S. Uemura, Angew. Chem. Int. Ed.2003,42,1495. (q) F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev.2004,104, 3079, and references cited therein. (r) Y. Liu, F. Song, Z. Song, M. Liu, B. Yan, Org. Lett.2005,7,5409.
90. Komeyama K.; Morimoto T.; Nakayama Y; Takaki K. Tetrahedron Lett.2007,48, 3259.
91. Komeyama K.; Mieno Y.; Yukawa S.; Morimoto T.; Takaki K. Chem. Lett.2007, 36,752.
92. Baldwin, J. E. J. Chem. Soc. Chem. Commun.1976,734.
93. Liu, Z.; Liu, L.; Shafiq, Z.; Wu, Y.; Wang, D.; Chen, Y. Synthesis 2007,13,1961.
94. Nishibayashi, Y.; Inada, Y.; Yoshikawa, M.; Hidai, M.; Uemura, S. Angew. Chem. Int. Ed.2003,42,1495.
95. Sanz R.; Martinez A.; Alvarez-Gutierrez J. M.; Rodriguez F. Eur. J. Org. Chem. 2006,1383.
96. Liu J.; Muth E.; Florke U.; Henkel G.; Merz K.; Sauvageau J.; Schwake E.; Dyker G. Adv. Synth. Catal.2006,348,456.
97. Srihari P.; Bhunia D. C.; Sreedhar P.; Mandal S. S.; Reddy J. S. S.; Yadav J. S. Tetrahedron Lett.2007,48,8120.
98. Nishibayashi Y.; Inada Y.; Yoshikawa M.; Hidai M.; Uemura S. Angew. Chem. Int. Ed.2003,42,1495.
99. (a) Zhan Z. P.; Cui Y. Y.; Liu H. J. Tetrahedron Lett.2006,47,9143; (b) Zhan Z. P.; Yu J. L.; Liu H. J.; Cui Y Y.; Yang R. F.; Yang W. Z.; Li J. P. J. Org. Chem.2006, 71,8298.
100. Zhan Z. P.; Yang W. Z.; Yang R. F.; Yu J. L.; Li J. P.; Liu H. J. Chem. Commun. 2006,3352.
101. Georgy M.; Boucard V.; Campagne J. M. J. Am. Chem. Soc.2005,127,14180.
102. Karunakar G. V.; Periasamy M. J. Org. Chem.2006,71,7463.
103. Kennedy-Smith J. J.; Young L. A.; Toste F. D. Org. Lett.2004,6,1325.
104. Dyker, G Handbook of C-H Transformations; Wiley-VCH: Weinheim,2005.
105. (a) Roesky, P. W. Angew. Chem., Int. Ed.2009,48,2. (b) Li, C. J. Acc. Chem. Res.2009,42,335. (c) Bergman, R. G. Nature 2007,446,391. (d) Campos, K. R. Chem. Soc. Rev.2007,36,1069. (e) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007,36,1173. (f) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev.2007,107, 174. (g) Godula, K.; Sames, D. Science 2006,312,67. (h) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev.2002,102,1731. (i) Dyker, G. Angew. Chem., Int. Ed. 1999,38,1698. (j) Shilov, A. E.; Shul'pin, G. B. Chem. Rev.1997,97,2879.
106. Norinder, J.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. J. Am. Chem. Chem. 2008,130,5858.
107. (a) Vallee, F.; Mousseau, J. J.; Charette, A. J. Am. Chem. Chem.2010,132,1514. (b) Liu, W.; Cao, H.; Lei, A. Angew. Chem. Int. Ed.2010,49,1.
108. Iovel, I.; Mertins, K.; Kischel, J.; Zapf, A.; Beller, M. Angew. Chem. Int. Ed. 2005,44,3913.
109. Li, Y. Z.; Li, B. J.; Lu, X. Y.; Lin, S.; Shi, Z. J. Angew. Chem. Int. Ed.2009,48, 3817.
110. (a) Li, Z.; Yu, R.; Li, H. Angew. Chem. Int. Ed.2008,47,7497. (b) Li, H.; He, Z.; Guo, X.; Li, W.; Zhao, X.; Li, Z. Org. Lett.2009,11, 4176.
111. (a) Peters AT, Freeman HS. Color chemistry: the design and synthesis of organic dyes and pigments. Barking, Essex:Appl Sci Publ Ltd; 1991. p193. (b) Gregory P. High-technology applications of organic colorants. New York and London: Plenum Press; 1991.p1.
112. Nolan, E. M.; Racine, M. E.; Lippard, S. J. Inorg. Chem.2006,45,2742.
113. Muniz, F. M.; Alcazar, V.; Simon, L.; Raposo, C.; Calle, E.; Moran, J. R. Eur. J. Org. Chem.2009,1009.
114. Hideu, T. Jpn. Tokkyo Koho JP,56005480; 1981 Chem. Abstr.1981,95,80922b. Lamberk RW, Martin JA, Merrett JH, Parkes KEB, Thomas GJ. PCT Int. Appl.
115. WO 9706178; 1997 Chem. Abstr.1997,126, P212377y.
116. Poupelin, J. P.; Saint-Rut, G.; Fussard-Blanpin, O.; Narcisse, G.; Uchida-Ernouf, G.; Lakroix, R. Eur. J. Med. Chem.1978,13,67.
117. Kraim, K.; Khatmi, D.; Saihi, Y.; Ferkous, F.; Brahimi, M. Chemom. Intel. Lab. Sys.2009,97,118.
118. Khosropour, A. R.; Khodaei, M. M.; Moghannian, H. Synlett.2005,955.
119. Rajitha, B.; Kumar, B. S.; Reddy, Y. T.; Reddy, P.; Sreenivasulu, N. Tetrahedron Lett.2005,46,8691.
120. Sarma, R. J.; Baruah, J. B. Dyes Pigments 2005,64,91.
121. Das, B.; Ravikanth, B.; Ramu, R.; Laxminarayana, K.; Rao, B. V. J. Mol. Catal. A:Chem.2006,255,74.
122. Pasha, M. A.; Jayashankara, V. P. Bioorg. Med. Chem. Lett.2007,17,621.
123. Nagarapu, L.; Kantevari, S.; Mahankhali, V. C.; Apuri, S. Catal. Commun.2007, 8,1173.
124. Bigdeli, M. A.; Heravi, M. M.; Mahdavinia, G. H. Catal. Commun.2007,8, 1595.
125. Saini, A.; Kumar, S.; Sandhu, J. S. Synlett.2006,1928.
126. Su W. K.; Yang D.; Jin C.; Zhang B. Tetrahedron Lett.2008,49,3391.
127. Singh, R.; Panda, G. Org. Biomol. Chem.2010,8,1097.
128. Li, H.; Yang, J.; Liu, Y. Li, Y. J. Org. Chem.2009,74,6797.
129. Yoshida H.; Watanabe M.; Fukushima H.; Ohshita J.; Kunai A. Org. Lett.2004,6, 4049.
130. Okuma, K.; Nojima, A.; Matsunaga, N.; Shioji, K. Org. Lett.2009,11,169.
131. Angeli, A. Gazz. Chim. Ital.1890,26,1793.
132. Scholtz, M. Ber. Dtsch. Chem. Ges.1912,45,734.
133. For recent reviews, see:(a) Micheal, J. P. Alkaloids 2001,55,91. (b) Micheal, J. P. Nat. Prod. Rep.2002,19,742.
134. Jorgensen, A. S.; Jacobsen, P.; Christiansen, L. B.; Bury, P. S.; Kanstrup, A.; Thorpe, S. M.; Naerum, L.; Wassermann, K. Bio. Med. Chem. Lett.2000,10, 2383.
135. Bermudez, J.; Fake, C. S.; Joiner, G F.; King, F. D.; Miner, W. D.; Sanger, G J. J. Med. Chem.1990,33,1924.
136. Gubin, J.; Lucchetti, J.; Mahaux, J.; Nisato, D.; Rosseels, G.; Clinet, M.; Polster, P.; Chatelain, P. J. J. Med. Chem.1992,35,981.
137. (a) Nash, R. J.; Fellows, L. E.; Dring, J. V.; Striton, C. H.; Carter,D.; Hegarty, M. P.; Bell, E. A. Phytochemistry 1988,27,1403. (b)Molyneux, R. J.; James, L. F. Science 1982,216,190.
138. Taguchi, T. U. S. Patent 0015614-A1,2001.
139. Wani, M. C; Bonman, P. E.; Lindley, J. T.; Wall, M. E. J. Med. Chem.1980,23, 554.
140.吴达,梁冰,冯志刚,师彦平。中兽医医药杂志,2003,42.
141. Chichibabin, A. E. Chem. Ber.1927,60,1607.
142. Borrows, E. T.; Holland, D. O.; Kenyon, J. J. Chem. Soc.1946,1069.
143. Bragg, D. R.; Wibberly, D. G. J. Chem. Soc.1963,3277.
144. Henrick, C. A.; Ritchie, E.; Taylor, W. C. Aust. J. Chem.1967,20,2467.
145. Wei, J.; Hu, Y.; Li, T.; Hu, H. J. Chem. Soc. Perkin trans.11993,2487.
146. Hou, J.; Hu, Y; Hu, H. Synth. Commun.199.8,28,3397.
147. Matsumoto, K.; Ogasawara, A.; Kimura, S.; Hayashi, N.; Machiguchi, T. Heterocycles 1998,48,861.
148. Kel'in A. V.; Sromek A. W.; Gevorgyan V. J. Am. Chem. Soc.2001,123,2074.
149. Kim J. T.; Butt J.; Gevorgyan V. J. Org. Chem.2004,69,5638.
150. Chernyak D.; Gadamsetty S. B.; Gevorgyan V. Org. Lett.2008,10,2307.
151. Chuprakov S.; Hwang F. W.; Gevorgyan V. Angew. Chem. Int. Ed.2007,46, 4757.
152. Chuprakov S.; Gevorgyan V. Org. Lett.2007,9,4463.
153. Yan, B.; Zhou, Y.; Zhang, H.; Chen, J. Liu, Y. J. Org. Chem.2007,72,7783.
154. Yan, B.; Liu, Y. Org. Lett.2007,9,4323.
155. Liu, Y.; Song, Z.; Yan, B. Org. Lett.2007,9,409.
156. Glamkowski, E. J.; Fortunato, J. M.; Spaulding, T. C.; Wilker, J. C.; Ellis, D. B. J. Med. Chem.1985,28,66.
157. Unangst, P. C.; Carethers, M. E.; Webster, K.; Janik, G. M.; Robichaud, L. J. J. Med. Chem.1984,27,1629.
158. Kamat, A. G.; Gadaginamath, G S. Indian J. Chem.1994,33,255.
159. Perregaard, J.; Arnt, J.; Boegesoe, K. P.; Hyttel, J.; Sanchez, C. J. Med. Chem. 1992,35,1092.
160. Cole, D. C.; Ellingboe, J. W.; Lennox, W. J.; Mazandarani, H.; Smith, D. L.; Stock, J. R.; Zhang, G. M.; Zhou, P.; Schechter, L. E. Bioorg. Med. Chem. Lett. 2005,15,379.
161. Li, Q.; Li, T. M.; Woods, K. W.; Gu, W. Z.; Cohen, J.; Stoll, V. S.; Galicia, T.; Hutchins, C.; Frost, D.; Rosenberg, S. H.; Sham, H. L. Bioorg. Med. Chem. Lett. 2005,15,2918.
162. Xu, H.; Liu, W. Q.; Fan, L. L.; Chen, Y.; Yang, L. M.; Lv, L.; Zheng, Y. T. Chem. Pharm. Bull.2008,6,720.
163. (a) For review, see:Lindley, J. Tetrahedron 1984,40,1433. (b) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc.1998,120,12459. (c) Ma, D.; Xia, C. Org. Lett.2001,3,2583. (d) Weingarten, H. J. Org. Chem.1964,29,3624. (e) Shimakawa, R. O.; Takenaka, S. Chem. Lett.1988,899. (f) Marcoux, J. F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc.1997,119,10539. (g) Cristau, H.; Cellier, P. P.; Spindler, J.; Taillefer, M. Chem. Eur. J.2004,10,5607. (h) Grasa, G A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem.2001,66,7729.
164. Ackermann, L.; Barfuber, S.; Potukuchia, H. K. Adv. Synth. Catal.2009,351, 1064.