含杂环二茂铁亚胺异环环钯化合物的合成及应用
详细信息    本馆镜像全文|  推荐本文 |  |   获取CNKI官网全文
摘要
本论文对环金属化反应和Heck反应的研究进展作了较详细的文献总结,在此基础上,对含杂环二茂铁亚胺异环环钯化合物的合成与应用进行了以下研究。
     一、含杂环二茂铁亚胺的合成与结构表征
     以二茂铁氨基衍生物和相应的呋喃甲醛、噻吩甲醛、吡啶甲醛、酰基二茂铁等为原料合成了一系列新型含杂环二茂铁亚胺衍生物(Scheme 1),并对这些化合物进行了元素分析、核磁共振、红外光谱、熔点等性质表征,其中化合物2a通过X-射线单晶衍射对其结构进行了确证。研究了不同结构的二茂铁亚胺的合成方法。
In this thesis, the progress made in the studies of both the cyclometallation and Heck reaction was reviewed in detail, on the basis of which the synthese and application of heteroannular cyclopalladated ferrocenylimines involving heterocyclic ring in Heck reactions were studied in the following aspects.
    1. Syntheses and structural characterization of novel ferrocenylimines containing heterocyclic ring
    A series of novel ferrocenylimines containing heterocyclic ring were synthesized by the condensation of furaldehyde, thiophene-2-carboxaldehyde, pyridyladehyde and formylferrocene with the corresponding aminoferrocene derivatives in the presence of different solvents (Scheme 1). The products were characterized by elemental analysis, IR, NMR spectra, and the molecular structure of the compound 2a was further confirmed by X-ray crystal structure determination. Synthetic methods of different ferrocenylimines were studied in this paper.
引文
1. W.C. Zeise, Ann. Phys., 1827, 9, 932.
    2. T.J. Kealy and P.J. Pauson, Nature, 1951, 168, 1039.
    3. G. Wilkison, M. Rosenblum, M. C. Whiting and R. B. Woodward, J. Am. Chem.??Soc., 1952, 74, 2125.
    4. H. Alper. J. Organomet. Chem. 1974, 80, 511.
    5. S.S. Grawford, G. Firestein, H. D. Kaesz, J. Organomet. Chem. 1975, 91, C57.
    6. J.C. Gaunt and B. L. Shaw, J. Organomet. Chem. 1975, 102, 511.
    7. A. Kasahara, T. Izumi and M. Maemura, Bull. Chem. Soc. Jpn., 1977, 50, 1878.
    8. V.I. Sokolov, L. L. Troitskaya and O. A. Reutov, J. Organomet. Chem. 1979, 182, 537.
    9. P. Castan, F. Dahan, S. Wimmer, F. L. Wimmer, J. Chem. Soc., Dalton Trans., 1990, 2971.
    10. P. R. R. Ranatunge-Bandarage, B. H. Robinson and Simpson, Organometallics, 1994, 13, 500.
    11. Y. J. Wu, S. Q. Huo, J. F. Gong, X. L. Xui, L. Ding, C. X. Du, Y. H. Liu and M. P. Song, J. Organomet. Chem. 2001, 637-639, 27.
    12. S. E Molnar and M. Orchin, J. Organomet. Chem. 1969, 16, 196.
    13. H. Onoue and I. Moritani, J. Organomet. Chem. 1972, 43, 431.
    14. H. Alper., J. Organomet. Chem. 1974, 80, 511.
    15. B. K. Dwivedi, B. Kiran, Synth. React. Inorg. Met. Org. Chem., 1986, 16, 715.
    16. E. M. Hodett, W. J. Dunn, J. Med. Chem., 1970, 13 (4), 768.
    17. E. W. Neuse, M. G. Meirim and N. F. Blom, Organometallics, 1988, 7, 2562.
    18. N. Motohashi, R. Meyer, S. R. Gollapudi and K. R. Bhattiprolu, J. Organomet. Chem. 1990, 398, 205.
    19. S. Q. Huo, Y. J. Wu, Y. Zhu, L. Yang, J. Organomet. Chem. 1994, 470, 17.
    20. Y. J. Wu, S. Q. Huo, Y. Zhu, L. Yang, J. Organomet. Chem. 1994, 481,235.
    21. Y. J. Wu, S. Q. Huo, X. A. Mao, H. Z. Yuan, Tetrahedron, 1994, 50, 10467.
    22. Y. J. Wu, S. Q. Huo, C. X.. Du, Y. Zhu, J. Organomet. Chem. 1994, 483, 139.
    23. S. Q. Huo, Y. Zhu, Y. J. Wu, J. Organomet. Chem. 1995, 490, 243.
    24. Y. J. Wu, Y. H. Liu, K. L. Ding, H. Z. Yuan, X. A. Mao, J. Organomet. Chem. 1995, 505, 37.
    25.刘元红,吴养洁,员红英,杨立,朱启秀,高等学校化学学报,1996,17,1225.26. Y. J. Wu, Y. H. Liu, L. Yang, Y. Zhu, Polyhedron, 1997,16, 335.
    
    27. C. Lopez, J. Sales, R. Zquiak, X. Solans, J. Chem. Soc, Dalton Trans., 1992, 221.
    
    28. R. Bosque, C. Lopez, J. Sales, X. Solans, M. Font-Bardia, J. Chem. Soc, Dalton Trans., 1994, 735.
    
    29. R. Bosque, M. Font-Bardia, C. Lopez, J. Sales, J. Silver, X. Solans, J. Chem. Soc, Dalton Trans., 1994, 747.
    
    30. R. Bosque, C. Lopez, J. Sales, X. Solans, J. Organomet. Chem. 1994, 483, 61.
    
    31. C. Lopez, R. Bosque, M. Font-Bardia, X. Solans, D. Tramuns, G. Fern, J. Silver, J. Chem. Soc, Dalton Trans., 1994, 3039.
    
    32. R. Bosque, C. Lopez, J. Sales, D. Tramuns, X. Solans, J. Chem. Soc, Dalton Trans., 1995, 2445.
    
    33. R. Bosque, C. Lopez, J. Sales, X. Solans, J. Silver, J. Chem. Soc, Dalton Trans., 1996,3139.
    
    34. C. Lopez, R. Bosque, X. Solans, M. Font-Bardia, J. Silver, G. Fern, J. Chem. Soc, Dalton Trans., 1995, 4053.
    
    35. C. Lopez, R. Bosque, J. Organomet. Chem. 1996, 524, 247.
    
    36. Y. J. Wu, S. Q. Huo, Y. Zhu, J. Organomet. Chem. 1995, 485, 161.
    
    37. Y. J. Wu, S. Q. Huo, C. X.. Du, L. Yang, J. Organomet. Chem. 1995, 490, 249.
    
    38. Y. J. Wu, S. Q. Huo, H. Z. Yuan, Y. H. Liu, Main Group Chemistry, 1996, 1, 253.
    
    39. Y. H. Liu, Y. J. Wu, S. Q. Huo, H. Z. Yuan, J. Organomet. Chem. 1997, 534, 7.
    
    40. Y. J. Wu, Y. H. Liu, X. L. Cui, H. Z. Yuan, X. A. Mao, Polyhedron, 1996, 15, 3315.
    
    41. K. H. Lin, M. P. Song, Y. Zhu, Y. J. Wu, J. Organomet. Chem. 2002, 660(2), 139.
    
    42. X. L. Hou, X. L. Cui, M. P. Song, X. Q. Hao, Y. J. WU, Polyhedron, 2003, 22, 1249.
    
    43. J. Higgius, J. Inorg. Biochem., 1993, 49, 149.
    
    44. R. Bosque, C. Lopez, J. Sales, J. Organomet. Chem. 1996, 471, 265.
    
    45. J. M. Birmingham, Chem. Eng. Prog., 1962, 58(10), 74.
    
    46. J. M. Birmingham, Advances in organometallic chemistry Acalemic: press, 1964, 2404.
    47. E. Kaminski, Z. Bentkowski, W. Pawlowski, Pol. Pat. 1981, 108252.
    48. K. Kishore and P. Rajalingan, J. Poym. Sci., Part, C: Polym. Lett., 1986, 24, 471.
    49. S. Tang, S. Xu, G. Hang, D. Tang, L. Li, J. Wang and H. Ding, Faming Zhuanli Shengqing Gongkai Shuomingshu, 1986, CN 85100494.
    50. I. P. Cherenyuk, V. P. Tverlokhlebov, I. V. Tselinskii, A. V. Sachivko and S. L. Levchenko, USSR Pat., 1982, 907030.
    51. B. O. Polishchuk, L. B. Polishchuk, L. A. Volf, K. Kh, Lazaridi and A. K. Spudulis, USSR Pat., 1980, 763386.
    52. S. Tang, S. Xu, G. Hang, D. Tang, L. Li, J. Wang and H. Ding, Faming Zhuanli Shenqing Gongkai Shuomingshu CN 85100494 (1986); CA 107, 40616 (1987).
    53. N. I. Kondrashkina, T. N. Zelekova, M. Z. Borodulina, B. I. Sazhin, Plast. Massy, 1982, 11, CA 97, 39982 (1982).
    54. V. I. Gulimov, T. P. Vishnyakova, I. D. Vlasova, Kauch. Rezina, 1987, 34; CA 107, 41442 (1987).
    55. H. Kato, Japan Pat. 1974, 74119941; CA 83, 29553 (1975).
    56. V. I. Sushkov, A. I. Vovozhin, S. S. Gusev, V. F. Firgin, L. Yu. Verhovodka and N. R. Prokopchuk,, Vvsokomol, Soedin, Ser. A, 1980, 22, 836.
    57. B. O. Polishchuk, L. B. Polishchuk, L. A. Volf, K. Kh. Lazaridi, and A. K. Spudulis, USSR Pat, 1980, 763386; CA 93,241115 (1980).
    58. P. N. Bartlett, R. G. Whitaker, M. J. Green and J. Frew, J. Chem. Soc., Chem. Comm., 1987, 1603.
    59. C. R. Simionescu, T. Lixandru, L. Tataru, J. Mazilu, M. Vata and Sp. Luca, J. Organomet. Chem. 1983, C43, 252.
    60. P. N. Bartlett, R. G. Whitaker, M. J. Green and J. Frew, J. Chem. Soc., Comm., 1987, 1603.
    61. A. Ratajczaj and A. Czech, Bull, Acad Pol. Sci., Ser. Sci., Chem., 1979, 27, 661.
    62. C. R. Simionescu, T. Lixandru, L. Tatasru, J. Mazilu, M. Vata and Sp. Luca, J. Organomet. Chem. 1983, 252, C 43.
    63. E. W. Neuse, M. G. Meirim and N. F. Blom, Organometallics, 1988, 7, 2562.
    64. H. Ernest, Increasing the yield of soyabeans [P], GB2078212, 06, Jan, 1982.65. Basarab, Gregory Stevern, Prearation of (zryalkyl and arylakylidene) amintriazzoles and imidazoles as agrochemical and, in part, medical fungicides, EP 283 254, 1988.
    66. A. Togni, R. Dorta, C. Kollner, G. Pioda, Pure & Appl. Chem. 1998, 70, 1477, and cited therein.
    67. K. Puntener, L. P. Schwink, Tetrahedron Lett. 1996, 37 (45), 8165.
    68. T. Sammakia, E. Stangeland, J. Organomet. Chem. 1997, 62, 6104.
    69. I. A. Volianskii, V. I. Boev, Khim-Farm. Zh. 1979, 13, 68.
    70. M. S. K. Youssef, Rev. Roum. Chim. 1981, 26, 1005.
    71. A. Houlton, R. M. G. Roberts, J. Silver, J. Organomet. Chem. 1991, 418, 107.
    72. L. V. Popova, V. N. Babin, et al, Appl. Organomet. Chem. 1993, 7, 85.
    73. Benito, M. Martinez-Manez, J. Paya, J. Sots, M. J. L. Tendero, E. Sinn, J. Organomet. Chem. 1995, 503, 259.
    74. Biidstein, M. Malaun, H. Kopacka, K. H. Ongania, K. Wurst, J. Organomet. Chem. 1999, 572, 177.
    75. I. R. Butler and J. L. roustan, Can. J. Chem. 1991, 69, 117 and cited therein.
    76. A. Gonzalez, P. Vazquez, T. Torres, Tetrahedron Lett. 1999, 40, 3263.
    77. H. Imahori, H. Yamada, Y. Sakata, Chem. Commun. 1999, 1165.
    78. K. Uosaki, T. Konodo, X. Q. Zhang, M. Yanagada, J. Am. Chem. Soc., 1997, 119, 8367.
    79. A. K. Burrel, W. Campbell, D. L. Officer, Tetrahedron Lett. 1997, 38, 1249.
    80. G.. B. Maiya, j. M. Barbe, K. M. Kadish, Inorg. Chem. 1989, 28, 2524.
    81. E. S. Schmidt, T. S. Calderwood, Tetrahedron:Asy. 1998, 9, 2377.1. Y.J. Wu, S. Q. Huo, J. F. Gong, X. L. Xui, L. Ding, C. X. Du, Y. H. Liu and M. E Song, J. Organomet. Chem. 2001, 637-639, 27-46.
    2. S.H. Huo, Y. J. Wu, C. X. Du, Y. Zhu, H. Z. Yuan, X. A. Mao, J. Organomet. Chem. 1994, 483, 139.
    3. Y.J. Wu, S. H. Huo, Y. Zhu, J. Organomet. Chem. 1995, 485, 161.
    4. Y.J. Wu, Y. H. Liu, H. Z. Yuan, X. A. Mao, J. Organomet. Chem. 1996, 519, 237.
    5. Y.J. Wu, Y. H. Liu and X. L. Cui, Polyhedron, 1996, 19, 3315.
    6. Y.J. Wu, Y. H. Liu, Polyhedron, 1997, 19, 335.
    7. Y.J. Wu, X. L. Cui, C. X. Du, W. L. Wang, R. Y. Guo, G. F. Chert, J. Chem. Soc., Dalton Trans., 1998, 3727.
    8. X.L. Cui, Y. J. Wu, C. X. Du, L. R. Yang, Y. Zhu, Tetrahedron:Asymmetry, 1999,??10, 1255.
    9. X.L. Cui, Y. J. Wu, L. R. Yang, Chinse ChemicalLetters, 1999, 10, 127.
    10.吴养洁,侯建军,廖新成,纪学学报,2001,59(11)1937.
    11. Y. J. Wu, J. J. Hou, H. Y. Jun, X. L. Cui, R. J. Yuan, J. Organomet. Chem. 2001, 637-639, 793.1. N.S. Kozlov, E. A. Kalennikovand and F. B. Kochereskaya, Zh. Org. Khim., 1974,??10, 1024.
    2.马怀让,杨秉勤,高胜利,李东行,张恒礼,张哓丽,西北大学学报,1992,20,46.
    3. N. Cully and W. F. Watts, Synth. Reat. 1hog. Met.-Org. Chem., 1980, 10, 289.
    4. P.J. Graham, R. V. Lindsey, G. W. Parshall, et al., J. Am. Chem. Soc. 1957, 79(13), 3416.
    5. F. Ossola, P. Tomasin, et al., lnorg. Chim. Acta. 2003, 353, 292.
    6. 同[2].
    7. M. Rosenblum and R. B. Woodward, J. Am. Chem. Soc., 1958, 80, 5443.
    8. P.J. Graham, R. V. Lindsey, G. W. Parshali, et al., J. Am. Chem. Soc. 1957, 79(13), 3416.
    9. F. Ossola, P. Tomasin, et al., Inorg. Chim. Acta. 2003, 353, 292.
    10. P. J. Graham, R. V. Lindsey, G. W. Parshall, et al., J. Am. Chem. Soc., 1957, 79 (13),3416.1. (a) A. W. Beng, A. J. P. White, D. J. Whilliams, Organometallics, 1996, 15, 3640.
    (b) C. Lopez, R. Bosque, D. Sainz, Organometallics, 1997, 16, 3261.
    2. K. Tain, H. Yashiro, M. Yoshida, et al., J. Organomet. Chem. 1994, 469, 229.
    3. (a) Ⅰ. Omae, Coord Chem. Rev., 1983, 137;
    (b) A. D. Ryabov, Chem. Rev., 1990, 90,403;
    (c) G. R. New Kome, W. E. Pucket, V. K. Gupta, et al., Chem. Rev., 1986, 86,451.
    4. H. Alper, J. Organomet. Chem. 1974, 80, 511
    5. J. Baena, J. Barro, J. Grane, J. Organomet. Chem. 1991, 408, 115.
    6. J. Higgius, J. lnorg. Biochem., 1993, 49, 149.
    7. B. H. Aw, P. H. Leung, A. J. P. Write, D. J. Williams, Organometallics, 1996, 15,3640.
    8. K. Loh, J. J. Vittai, P. H. Leung, Tetrahedron: Asymmetry, 1998, 9, 423.
    9. F. I. Luo, A. Jeevananda, M. K. Basu, Tetrahedron Lett., 1998, 39, 7979.
    10. D. A. Albisson. R. B. Bedford, P. N. Scally, Tetrahedron Left., 1998, 39, 9793.
    11. F. Cohen, L. E. Overman, Tetrahedron: Asymmetry, 1998, 9, 321.
    12. J. Higgius, J. Inorg. Biochem, 1993, 49, 149.
    13. S. P. Molnar and M. Orchin, J. Organomet. Chem., 1969, 16, 196.
    14. S. Q. Huo, Y. J. Wu, Y. Zhu, L. Yang, J. Organomet. Chem., 1994, 470, 17.
    15. Y. J. Wu, S. Q. Huo, Y. Zhu, L. Yang, J. Organomet. Chem., 1994,481, 235.
    16. S. Q. Huo, Y. J. Wu, X. A. Mao, H. Z. Yuan, Tetrahedron, 1994, 50, 10467.
    17. S. Q. Huo, Y. J. Wu, C. X. Du, Y. Zhu, H. Z. Yuan, X. A. Mao, J. Organomet. Chem., 1994, 483, 139.
    18. Y. J. Wu, Y. H. Liu, K. L. Ding, H. Z. Yuan, X. A. Mao, J. Organomet. Chem., 1995, 505,37.
    19. Y. J. Wu, S. Q. Huo, J. F. Gong, X. L. Xui, L. Ding, C. X. Du, Y. H. Liu and M. P. Song, J. Organomet. Chem. 2001, 637-639, 27.
    20. Y. J. Wu, Y. H. Liu, X. L. Cui, H. Z. Yuan, X. A. Mao, Polyhedron, 1996, 15,3315.
    21. Bosque, C. Lopez, J. Sales, J. Organomet. Chem. 1996, 471,265.22. J. C. Gaunt and B. L. Shaw, J. Organomet. Chem., 1975, 102, 511.
    23. A. Kasahara, T. Izumi and M. Maemura, Bull. Chem. Soc. Jpn., 1977, 50, 1878.
    24. S. Q. Huo, Y. J. Wu, C. X. Du, Y. Zhu, H. Z. Yuan, X. A. Mao, J. Organomet. Chem., 1994, 483, 139.
    25. M. Rosenblum, J. Am. Chem. Soc., 1958, 80, 5443.
    26. M. Rosenblum, Chemistry and lndustry, 1958, 953.
    27. M. Rosenblum, J. Am. Chem. Soc., 1959, 81, 4530.
    28. M. Rosenblum, Chemistry of the Iron Group Metallocences. New Youk:Willey-Interscience, 1965.
    29.洪山海,光谱解析法在有机化学中的应用,北京:科学出版社,1981.
    30. (a) P. J. Graham, R. V. Lindsey, G. W. Parshall, et al., J. Am. Chem. Soc. 1957, 79 (13), 3416. (b) F. Ossola, P. Tomasin, et ai., Inorg. Chim. Acta. 2003, 353, 292.
    31. S. Q, Huo, Y. J. Wu, C. X. Du, Y. Zhu, H. Z. Yuan, X. A. Mao, J. Organomet. Chem., 1994, 483 139.
    32. F. Ossola, P. Tomasin, et al., Inorg. Chim. Acta. 2003, 353, 292.
    33. E. B. Moynahan, F. D. Popp, M. F. Werneke, J. Organomet. Chem., 1969, 19 (1), 299.
    34. V. I. Sokolov, L. L. Troitskaya, O. A. Reutov, 1979, 182(4), 537.
    35. M. M. Bagga, W. T. Flannigan, G. R. Konx, et al, J. Chem. Soc. 1969, 11, 1534.
    36. (a) J. M. Duff and B. L. Shaw, J. Chem. Soc. Dalton Trans., 1972, 2219;
    (b) J. M. Duff, B. E. Mann, B. L. Shaw, B. Turtle, J. Chem. Soc. Dalton Trans., 1974, 139.
    37. E. J. Corey, S. M. Albonico, K. T. U. Schaafu, et al, J. Am. Chem. Soc. 1971, 93 (6), 1491.
    38. V. I. Sokolov, L. L. Troitskaya, N. S. Khrushchova, J. Organomet. Chem., 1983, 250(1), 439.
    39. V. I. Sokolov, L. L. Troitskaya, O. A. Reutov, J. Organomet. Chem., 1979, 182(4), 537.
    40. S. Trofimenko, Inorg. Chem. 1973, 12 (6), 1215.
    41.江焕峰,张伦,陈新兰,化学试剂,1997,19(3),131.1. C. Lopez, J. Sales, X. Solans, R. Zquiak, J. Chem. Soc. Dalton Trans., 1992, 2321.
    2. R. Bosque, C. Lopez, J. Sales, X. Solans, M. Font-bardia, J. Chem. Soc. Dalton Trans., 1994, 735.
    3. R. Bosque, M. Font-bardia, C. Lopez, J. Sales, X. Solans, J. Silver, J. Chem. Soc. Dalton Trans., 1994, 746.
    4. C. Lopez, R. Bosque, X. Solans, M. Font-bardia, D. Tramuns, G. Fern, J. Silver, J. Chem. Soc. Dalton Trans., 1994, 3039.
    5. R. Bosque, C. Lopez, J. Sales, Inorg. Chim. Acta., 1996, 244, 141.
    6. C. Lopez, R. Bosque, X. Solans, M. Font-bardia, New J. Chem. 1998, 22, 977.
    7. W.A. Henderson, C. A. Screuli, J. Am. Chem. Soc., 1960, 82, 5791.8. X. M. Zhao, X. Q. Hao, B. Liu, M. L. Zhang, M. P. Song, Y. J. Wu, J. Organomet. Chem., 2006, 691, 255-260.
    9. C. Lopez, R. Bosque, X. Solans, M. Font-bardia, New J. Chem. 1996, 20, 1285.1. W.A. Herrmann, V. P. W. Bohm, C. P. Reisinger, J. Organomet. Chem. 1999, 576, 23.
    2. S. Brase, A. de Meijere, F. Diederich, P. J. Stang (Eds.), Metal Catalyzed Cross-coupling Reaction, Wiley-VCH, 1988, p. 99.
    3. (a) J. G. de Vries, Can. J. Chem. 2001, 1086;
    (b) R. A. de Vries, P. C. Vosejpka, M. L. Ash, F. E. Herkes (Ed.), Catalysis of Organic Reactions, Chem. Ind. 1998,??75, 467.
    4. A.B. Dounay, L. E. Overman, Chem. Rev. 2003, 103, 2945.
    5. W.A. Herrmann, C. Brossmer, C. P. Reisinger, T. H. Riermeier, K. Ofele, M. Belier, Chem. Eur. J. 1997, 3, 1357.
    6. J. Tsuji, Sen-I Kinzoku-ga-hiraku Yuki-gosei (Organic Synthesis Extended with Transition Metals), Kagaku Dojin, Tokyo, 1997.
    7. J.E. Plevyak, P. E. Heck, J. Org. Chem. 1978, 43, 2454.
    8. R. Franzen, Can. J. Chem. 2000, 78, 957.
    9. T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn. 1971, 44, 581.
    10. R.F. Heck, J. P. Jr. Noiley, J. Org. Chem. 1972, 37, 2320.
    11. (a) W. A. Herrmann, C. Brossmer, K. Ofele, C. P. Reisinger, et al., Angew. Chem. lnt. Ed. Engl., 1995, 34, 1844;
    (b) B. L. Shaw, S. D. Perera, Chem. Commun., 1998, 1863;
    (c) F. Miyazaki, K. Yamaguchi, M. Fischer, et al., Tetrahedron Lett., 1999, 40, 7379.
    12. W.E. Herrmann, M. Elison, J. Fischer, et al., Angew. Chem. lnt. Ed. Engl., 1995, 34, 2371.
    13. M. Nowotny, U. Nanefeld, H. V. Koningsveld, T. Mascheyer, Chem. Commun., 2000, 11877.
    14. T.A. Mitsudo, M. Takagi, S. W. Zhang, Y. Watanabe, J. Organomet. Chem. 1992, 423, 405.
    15. H.A. Dieck, R. F. Heck, J. Am. Chem. Soc., 1974, 96, 1133.
    16. (a) P. S. Stephen, Tetrahedron, 1998, 54(2): 263-303;
    (b) P. B. Irina, Pure and Appl Chem., 1997, 4: 471-476;
    (c) 杜卫红,安忠维,徐茂梁,分子催化,1997, 11 (1):72-80.
    17. B.E. Segelstein, T. W. Butler, B. L. Chenard, J. Org. Chem., 1995, 60 (1): 12-13.
    18. D. F. O. Keefe, M. C. Dannock, S. M. Marcuccio, Tetrahedron Lett., 1992, 33 (44): 6679-6681.
    19. T.I. Wallow, B. M. Novak, J. Org. Chem., 1994, 59: 5034-5037.
    20. A. Spencer, J. Organomet. Chem. 1983, 258, 101.
    21. Y. Ben-David, M. Portnoy and D. Milstein, J. Am. Chem. Soc., 1989, 111, 8742.
    22. Y. Ben-David, M. Portnoy and D. Milstein, Chem. Commun., 1989, 1816.
    
    23. Y. Ben-David, M. Portnoy, M. Gozin and D. Milstein, Organometallics, 1992, 77, 1995.
    
    24. A. F. Littke and G. C. Fu, J. Org. Chem., 1999, 64: 10.
    
    25. M. T. Teetz, G. Lohmer and R. Schwickardi, Angew. Chem. Int. Ed., 1998, 37, 481.
    
    26. J. J. Bozell and C. E. Voght, J. Am. Chem. Soc, 1988,110, 2655.
    
    27. C. Yang, H. M. Lee and S. P. Nolan, Org. Lett., 2001, 3, 1511.
    
    28. A. L. Boyes, I. R. Butler and S. C. Quayle, Tetrahedron Lett., 1998, 39, 7763.
    
    29. M. T. Reetz, E. Westermann, R. Lohmer and G. Lohmer, Tetrahedron Lett., 1998, 39, 8449.
    
    30. M. Moreno-Manas, R. Pleixats and S. Villarroya, Organometallics, 2001, 20, 4524.
    
    31. T. Jeffery, Tetrahedron Lett., 2000, 41, 8445
    
    32. R. F. Heck and J. P. Nolley, J. Org. Chem. 1972, 14, 2320.
    
    33. W. A. Herrmann, V. P. W. Bohm, C. P. J. Reisinger, Organomet. Chem., 1999, 576, 23.
    
    34. W. A. Herrmann, C. Brossmer, K. Olele, C. P. Reisinger, T. Priermeier, M. Beller and H. Fischer, Angew. Chem. Int. Ed, 1995, 34, 1844.
    
    35. S. Gibson, D. F. Foster, G. R. Eastham, R. P. Tooze and D. J. Cole-Hamilton, Chem. Commun., 2001, 779.
    
    36. A. Zapf and M. Beller, Chem. Eur. J., 2001, 7, 2908.
    
    37. F. Miyazaki, K. Yamaguchi and M. Shibasaki, Tetrahedron Lett., 1999, 40, 17,19.
    
    38. D. A. Albisson, R. B. Bedford and P. N. Scully, Tetrahedron Lett., 1998, 39, 9793.
    
    39. B. L. Shaw, S. D. Perera and E. A. Staley, Chem. Commun., 1998, 1361.
    
    40. M. Ohff, A. Ohff, M. E. Van der Boom and D. Milstein, J. Am. Chem. Soc, 1997, 779,11687.
    
    41. K. Kiewel, Y. Liu, D. E. Bergbreiter and G. A. Sulikowski, Tetrahedron Lett., 1999, 40, 8945.
    
    42. M. Ohff, A. Ohff and D. Milstein, Chem. Commun., 1999, 357.
    
    43. M. Nowotny, U. Hanefeld, H. Van Koningsveld and T. Maschmeyer, Chem. Commun., 2000 1877.
    
    44. X. Gai, R. Grigg, M. I. Ramzan, V. Sridharan, S. Collard and J. E. Muir, Chem. Commun., 2000, 2053.
    
    45. I. P. Beleskaya, A. N. Kashin, N. B. Karlstedt, A. V. Mitin, A. V. Cheprakov and G. M. Kazankov, J. Organomet. Chem. 2001, 622,89.
    
    46. A. S. Gruber, D. Zim, G. Ebeling, A. L. Monteiro and J. Dupont, Org. Lett., 2000, 2, 1287.
    
    47. D. E. Bergbreiter, P. L. Osburn and Y. Liu, J. Am. Chem. Soc, 1999, 121, 9531.
    
    48. W. A. Herrmann, M. Elison, J. Fischer, C. Kocher, G. R. Artus, Angew. Chem. Int. Ed, Engl, 1995, 34, 2371.
    
    49. J. Schwarz, V. P. W. Bohm, M. G. Gardiner, M. Grosche, W. A. Herrmann, W. Hieringer and G. Raudschl-Sieber, Chem. Eur. J., 2000, 1773.
    
    50. M. S. Anson, A. R. Mirza, L. Tonks and J. M. Williams, Tetrahedron Lett., 1999, 40, 7147.
    
    51. L. Djakovitch and K. Koehler, J. Am. Chem. Soc, 2001, 123, 5990.
    
    52. S. B. Jang, Tetrahedron Lett., 1997, 38 (25): 4421 -4424.
    
    53. S. B. Jang, Tetrahedron Lett., 1997, 38 (10): 1793-1796.
    
    54. S. Brase, B. waegellb, A. de Meijere, Synthese of Syn. Org. Chem., 1998, 2, 148-151.
    
    55. B. M. Choudhary, R. M. Sanma, K. K. Rao, Tetrahedron, 1992, 48, 719-726.
    
    56. R. K. Ramchandani, B. S. Uphade, M. P. Viod, Chem. Common, 1997, 21, 2071-2072.
    
    57. A. L. Casalnuovo and J. C. Calabrese, J. Am. Chem. Soc., 1990,112, 4324.
    
    58. S. Lemaire-Audoire, M. Savignac, C. Dupuis and J. P. Genet, Tetrahedron Lett., 1996, 37, 2003.
    
    59. H. Dibowski and F. P. Schmidtchen, Tetrahedron, 1995, 51, 2325.
    
    60. A. Hesser, O. Stelzer, H. Dibowski, K. Worm and F. P. Schmidtchen, J. Org. Chem., 1997, 62, 2326.
    61. F. Eymery, P. Burattin, F. Mathey and P. Savignac, Eur. J. Org. Chem., 2000, 2425.
    62. D.E. Bergbreiter and Y. S. Liu, Tetrahedron Lett., 1997, 38, 7843.
    63. W. A. Hermnna, C. Brossmer, K. Ofele, et al., Angew. Chem. Int. Ed., Engl., 1995, 34, 1844-1848.
    64. M. T. Reetz, G. Lohmer, R. Schwickardi, Angew. Chem. Int. Ed., Engl., 1998, 37 (4), 481-483.
    65. Vittoriob Farina, Pure and Appl. Chem., 1996, 68 (1): 73-78.
    66. E. Shirakaw, H. Yoshida, H. Takaya, Tetrahedron Lett., 1997, 38 (21), 3759-3762.
    67. F. Mercier, F. Laporate, L. Ricard, et al., Angew. Chem. Int. Ed., Engl., 1997, 36 (21), 2364-2366.
    68. B. Betzemier, P. Knochel, Angew. Chem. Int. Ed., Engl., 1997, 36 (23), 2623-2624.
    69. C. G. Bletter, W. A. Konig, W. Stenzel, et al., J. Org. Chem., 1999, 64, 3885-3890.
    70.陈新兵、安忠维、刘骞峰等,合成化学,2000,8(4),291-293.
    71. W. Cabri and I. Candiani, Acc. Chem.Res., 1995, 28, 2.
    72. V. P. W. Bohm and W. A. Herrmann, Chem. Eur. J., 2001, 7, 4149.
    73. T. Rosner, J. L. Bars, A. Pfaltz and D. G. Blackmond, J. Am. Chem. Soc., 2001, 123, 1848.
    74. M. Catellani, F. Frignani and A. Rangoni, Angew. Chem. Int. Ed, Engl., 1997, 36, 119.
    75. T. Rosner, A. Pfaltz and D. G. Blackmond, J. Am. Chem. Soc., 2001, 123, 4621.
    76. C. Amatore, E. Carre, A. Jutand and M. Mbarki, Organometallics, 1995, 14, 1818.
    77. F. Ozawa, A. Kubo and T. Hayashi, Chem. Left., 1992, 11, 2177.
    78. C. Amatore, A. Jutand and M. A. Mbarki, Organometallics, 1992, 11, 2177.
    79. M.T. Reetz and E. Westmann, Angew. Chem. lnt. Ed., 2000, 39, 165.
    80. P.A. Mclaughlin and J. G. Verkade, Organometallics, 1998, 17, 5937.81. P. Roffia, G. Gregorio, F. Conti and G. F. Pregaglia, J. Mol. Catal., 1977, 2, 191.
    82. V.V. Grushin and H. Aiper, Organometallics, 1993, 12, 1890.
    83. M.R. Mason and J. G. Verkade, Organometallics, 1992, 11, 2212.
    84. M. Loele, G. Ortaggi, M. Scarsella and G. Sleiter, Polyhedron, 1991, 10, 2475.
    85. V.V. Grushin, J. Am. Chem. Soc., 1999, 121, 5831.
    86. C. Amatore, A. Jutand and M. J. Medeiros, New J. Chem., 1996, 20, 1143.
    87. A. Jutand and A. Mosleh, Organometallics, 1995, 14, 1810.
    88. A.C. Albeniz, P. Espinet and Y. S. Lin, Organometallics, 1995, 14, 2977.
    89. M. Ludwig, S. Stromberg, M. Svensson and B. Akermark, Organometallics, 1999, 18, 970.
    90. S. Brase, J. Rumper, K. Voigt, S. Albecq, G. Thurau, R. Villard, B. Waegell and A. de Meijere, Organometallics, 1995, 14, 2977.
    91. F.E. Meyer, P. J. Parsons and A. de Meijere, Organometallics, 1991, 56, 6487.
    92. Y. Zhang and E. Negishi, J. Am. Chem. Soc., 1999, 121, 5831.
    93. C.H. Liu, C. H. Cheng, M. C. Cheng and S. M. Peng, Organometallics, 1994, 13, 1832.
    94. A. Spencer, J. Organomet. Chem. 1982, 240, 209.
    95. W. Cabri, I. Canadiani, A. Bedeschi and R. Santi, J. Org. Chem., 1993, 58, 7421.
    96. B. L. Shaw, S. D. Perera and E. A. Staley, Chem. Commun., 1998, 1361.
    97. K.R. Seddon, J. Chem. Tech. Biotechnol. 1997, 68, 351.
    98. L. Xu, W. Chen and J. Xiao, Organometallics, 2000, 19, 1123.
    99. L. Xu, W. Chen, J. Ross and J. Xiao, Org. Lett, 2001, 3, 295.
    100. A. J. Carmichael, M. J. Earle, J. D. Holbrey, P. B. Mccormac and K. R. Seddon, Org. Lett, 1999, 1,997.
    101. W. A. Herrmann and V. P. W. Bohm, J. Organomet. Chem., 1999, 572, 141.
    102. V. Calo, A. Nacci, L. Lopez and A. Napola, Tetrahedron Left., 2001, 42, 4701.
    103. H. Hagiwara, Y. Shimizu, T. Hoshi, T. Suzuki, M. Ando, K. Ohkubo and C. Yokoyama, Tetrahedron Lett., 2001, 42, 4349.
    104. V. P. W. Bohm and W.A. Herrmann, Chem. Eur. J., 2000, 6, 1017.
    105. Wang Shen, Tetrahedron Lett., 1997, 38 (32), 5575-5578.
    106. A. Sundermann, O. Uzan and J. M. L. Martin, Chem. Eur. J., 2001, 1703.
    
    107. M. Larhed, C. Moberg, A. Hallberg, Acc. Chem. Res. 2002, 35, 717.
    
    108. K. Olofsson, A. Hallberg, M. Larhed, Microwaves in Organic Synthesis, ed. Loupy, A. Wiley-VCH, Weinheim, 2002, ch. 11.
    
    109. S. B. Jang, Tetrahedron Lett., 1997, 38 (25): 4421-4424.
    
    110. W. A. Herrmann, M. Elison, J. M. Fisheretal, et al., Angew. Chem. Int. Ed., Engl., 1995, 34 (21), 2371-2374.
    
    111. M. Larhed, A. Hallberg, J. Org. Chem., 1996, 61, 9582.
    
    112. S. Hillers, S. Sartori, O. Reiser, J. Am. Chem. Soc, 1996,118, 2087.
    
    113. S. Iyer, C. Ramesh, A. Sarkar and P. P. Wadgaonkar, Tetrahedron Lett., 1997, 38, 8113.
    
    114. S. A. Lebedev, V. S. Lopatina, E. S. Petrov and I. P. Beletskaya, J. Organomet. Chem., 1988, 344, 253.
    
    115. S. Iyer, C. Ramesh and A. Ramani, Tetrahedron Lett., 1997, 38, 8355.
    
    116. S. Condon-Gueugnot, E. Leonel, J. Y. Nedelec and J. Perichon, J. Org. Chem., 1995, 60, 7684.
    
    117. S. Iyer, J. Organomet. Chem., 1995, 490, C27.
    
    118. A. A. Kelkar, Tetrahedron Lett, 1996, 37, 8917.
    
    119. T. A. Mitsudo, M. Takagi, S. W. Zhang and Y. Watanabe, J. Organomet. Chem., 1992, 423, 405.
    
    120. T. Ishiyama and J. Hartwig, J. Am. Chem. Soc, 2000,122, 12043.
    1.晓岚编译,农药的发展与展望,农药丛译,1995,3.
    2.特开昭,63-57565[专,日]/三井东庄化学公司,1988,3,12,CA(109):75153.
    3.特开昭,63-57565[专,日]/大赛尔化学公司,1987,10,30-19,CA(109):144600.
    4.特开昭,89-139557[专,日]/保土治化学公司-1987,10,30-19,CA(109):14460.
    5.刘长玲,农药译丛,1995,1,30.
    6.(a) 张淑英,李勇,郭燕文等,乙醛酸衍生物的研究进展,化学研究与应用, 2000,12(2),125-131;
    (b) 中永存,邹淑静,对羟基苯乙酰胺合成上艺改进,中国医药工业杂志,1995,26(9),416-417.
    7. (a) E. I. Edwards, R. Epton, M. George, Organometallic derivatives of penicillins and cephalosporins anew class of sem i-synthetic antibiotics, J. Organomet. Chem., 1975, 85(1), c_(23)-c_(25).
    (b) 戴朝峰,惠新平,张林梅等,含二茂铁基的氨基硫脲均三唑和恶二唑的合成,兰州大学学报 (自然科学版),2002,38(5),51-57.
    8. (a) P. J. Graham, R. V. Lindsey, G. W. Parshall, et al., Some acyl ferrocenes and their reaction, J. Am. Chem. Soc. 1957, 79 (13), 3416-3420.
    (b) F. Ossola, P. Tomasin, et al., Synthesis, structure and properties of new ferrocene- containing compounds, Inorg. Chim. Acta. 2003, 353,292-300.
    9. (a) M. Rosenblum, R. B. Woodward, The structure and chemistry of ferrocene.III. Evidence pertaining to the ring totational barrier, J. Am. Chem. Soc. 1958, 80 (20), 5443-5449. (b) K. L. Rinehart, Jr. K. L. Motz, S. Moon, Organic chemistry of ferrocene. I . the acetylation of dialkylferrocenes, J. Am. Chem. Soc. 1957, 79 (11), 2749-2754.
    
    10. G. Besenyei, L. Parkanyi, S. Nemeth, L. I. Simandi, J. Organomet. Chem. 1998, 563,81-86