吡啶C-H键活化及功能化
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摘要
在本论文中,作者从事了金属钯配合物的合成及催化活性的研究,其中包括吡啶氧化物C-H活化及功能化,以及不对称的C-C偶联反应。
第一章,作者详细描述了近年来以过渡金属为催化剂,通过吡啶类化合物的直接C-H活化及功能化合成一系列在医药、生物、农药等领域占有重要地位的含吡啶结构的杂环化合物。
第二章,作者以醋酸钯为催化剂,碳酸银为氧化剂,通过吡啶氧化物2-位及吲哚3-位的两次C-H活化,完成了吡啶氧化物与吲哚的氧化偶联反应,合成了一系列3-(2-吡啶氧化物)吲哚类化合物。动力学同位素效应显示,吡啶氧化物的C-H活化包含在反应的决速步中。
第三章,作者设计、合成、表征了一类基于含噁唑啉结构的NNN三齿类配体的二价钯配合物。在催化不对称Suzuki-Miyaura偶联反应中,该类钯配合物具有良好的催化活性及立体选择性。
In this dissertation, my aim is to study synthesis and catalytic application ofpalladium complexes, including pyridine N-oxide C-H functionalization andenantioselectivity C-C coupling reaction.
Transition-metal-catalyzed C-H activation and functionalization of pyridinemoiety was reviewed in Chapter 1. By this way, a series of pyridine derivates wereprepared, which play great roles in pharmaceutical and pesticide.
Chapter 2 described that Pd(II)-catalyzed oxidative coupling between pyridineN-oxides and N-substituted indoles via two-fold C-H bond activation has beenachieved using Ag2CO3 as an oxidant. Kinetic Isotope Effect (KIE) indicates that thecleavage of the N-oxide C-H bond is involved in the rate-determining step.
In Chapter 3, a series of palladium complexes bearing pincer chairal oxazolineligand were designed and synthesized. In asymmetric Suzuki-Miyaura couplingreaction, these palladium complexes have showed high efficiency andenantioselectivity.
第一章,作者详细描述了近年来以过渡金属为催化剂,通过吡啶类化合物的直接C-H活化及功能化合成一系列在医药、生物、农药等领域占有重要地位的含吡啶结构的杂环化合物。
第二章,作者以醋酸钯为催化剂,碳酸银为氧化剂,通过吡啶氧化物2-位及吲哚3-位的两次C-H活化,完成了吡啶氧化物与吲哚的氧化偶联反应,合成了一系列3-(2-吡啶氧化物)吲哚类化合物。动力学同位素效应显示,吡啶氧化物的C-H活化包含在反应的决速步中。
第三章,作者设计、合成、表征了一类基于含噁唑啉结构的NNN三齿类配体的二价钯配合物。在催化不对称Suzuki-Miyaura偶联反应中,该类钯配合物具有良好的催化活性及立体选择性。
In this dissertation, my aim is to study synthesis and catalytic application ofpalladium complexes, including pyridine N-oxide C-H functionalization andenantioselectivity C-C coupling reaction.
Transition-metal-catalyzed C-H activation and functionalization of pyridinemoiety was reviewed in Chapter 1. By this way, a series of pyridine derivates wereprepared, which play great roles in pharmaceutical and pesticide.
Chapter 2 described that Pd(II)-catalyzed oxidative coupling between pyridineN-oxides and N-substituted indoles via two-fold C-H bond activation has beenachieved using Ag2CO3 as an oxidant. Kinetic Isotope Effect (KIE) indicates that thecleavage of the N-oxide C-H bond is involved in the rate-determining step.
In Chapter 3, a series of palladium complexes bearing pincer chairal oxazolineligand were designed and synthesized. In asymmetric Suzuki-Miyaura couplingreaction, these palladium complexes have showed high efficiency andenantioselectivity.
引文
[1] Anastas P, Eghbali N, Chem Soc Rev[J], 2010, 39, 301-312.
[2] Ritleng V, Sirlin C, Pfeffer M, Chem Rev[J], 2002, 102, 1731-1770.
[3] Tsuji J, Palladium Reagents and Catalysis: Innovations in Organic Synthesis, John Wiley,Chichester1995.
[4] Negishi E, de Meijere A Eds,Handbook of Organopalladium Chemistry for Organic Synthesis,John Wiley＆Sons , Inc: New York,2002;Vol.1-2.
[5] Tsuji J, Palladium Reagents and Catalysis: new Persspectives for the 21st Centry, 2nd ed. JohnWiley＆Son Ltd, 2004.
[6] Zaitsev V G., Shabashov D, Daugulis O, J Am Chem Soc[J], 2005,127, 13154-13155.
[7] Carey J S, Laffan D, Thomson C, etal. Org Biomol Chem[J], 2006, 4, 2337-2347.
[8] Campeau L–C, Rousseaux S, Fagnou K, J Am Chem Soc[J], 2005, 127, 18020-18021.
[9] Leclerc J–P, Fagnou K, Angew Chem Int Ed[J], 2006,45,7781-7786.
[10] Kanyiva K S, Nakao Y, Hiyama T, Angew Chem Int Ed[J], 2007,46,8872-8874.
[11] Campeau L–C, Schipper D J, Fagnou K, J Am Chem Soc[J], 2008, 130, 3266-3267.
[12] Zhao D, Wang W, Yang F, et al. Angew Chem Int Ed[J],2009,48,3296-3300.
[13] Campeau L–C, Stuart D R, Leclerc J–P, J Am Chem Soc[J], 2009, 131, 3291-3306.
[14] Huestis M P, Fagnou K, Org Lett[J], 2009,11,1357-1360.
[15] Schipper D J, El-Salfiti M, Whipp C J, etal. Tetrahedron[J], 2009,65,4977-4983.
[16] Larivée A, Mousseau J J, Charette A B, J Am Chem Soc[J],2008,130,52-54.
[17] Cho S H, Hwang S J, Chang S, J Am Chem Soc[J], 2008, 130, 9254-9256.
[18] Deng G ,Ueda K, Yanagisawa S, et al. Chem Eur J[J], 2009,15,333-337.
[19] Medley J W, Movassaghi M, J Org Chem[J], 2009,74,1341-1344.
[20] Wu J, Cui X, Chen L, etal. J Am Chem Soc[J], 2009,131,13888-13889.
[21] Patureau F W, Glorius F, Angew Chem Int Ed[J], 2011,50,1977-1979.
[22] Seiple I B, Su S, Rodriguez R A, etal. J Am Chem Soc[J],2010,132,13194-13196.
[23] Minisci F, Vismara E, Fontana F, Heterocycles[J], 1989, 28, 489-519.
[24] Godula K, Sezen B, Sames D, J Am Chem Soc[J], 2005,127,3648-3649.
[25] Nakao Y, Kanyiva K S, Hiyama T, J Am Chem Soc[J], 2008,130,2448-2449.
[26] Lewis J C, Bergman R T, Ellman J A, J Am Chem Soc[J], 2007,129,5332-5333.
[27] Tan K L, Bergman R G, Ellman J A , J Am Chem Soc[J], 2002,124, 3202-3203.
[28] Lewis J C, Wiedemann S H, Bergman R G, etal. Org Lett[J], 2004, 6, 35-38.
[29] Tan K L, Bergman R G, Ellman J A, J Am Chem Soc[J], 2001,123, 2685-2686.
[30] Wiedemann S H, Lewis J C, Ellman J A, etal. J Am Chem Soc[J], 2006, 128, 2452-2462.
[31] Li B–J,Yang S–D, Shi Z -J, Synlett[J],2008, 949-957.
[32] Tobisu M, Hyodo I, Chatani N, J Am Chem Soc[J], 2009,131,12070-12071.
[33] Geissman T A, Schlatter M J, Webb I D, etal. J Org Chem[J], 1946, 11, 741-750.
[34] Berman A M, Bergman R G, Ellman J A, J Org Chem[J], 2010,75,7863-7868.
[35] Gürbüz N, Ozdemir I, Cetinkaya B, Tetrahedron Lett. 2005, 46, 2273–2277.
[36] Lafrance M, Rowley C N, Woo T K, etal. J Am Chem Soc[J], 2006,128, 8754–8756.
[37] Lafrance M, Shore D, Fagnou K, Org Lett[J], 2006, 8, 5097–5100.
[38] Berman A M, Lewis J C, Bergman R G, J Am Chem Soc[J], 2008, 130, 14926-14927.s
[39] Nakao Y, Yamada Y, Kashihara N, J Am Chem Soc[J], 2010,132,13666-13668.
[40] Wasa M, Worrell B T, Yu J–Q, Angew Chem, Int Ed[J], 2010,49,1275-1277.
[41] Babu Y S, Rowland R S, Chand P, etal. US Patent No 6699994, 2004.
[42] Wasa M, Engle K M, Yu J -Q, J Am Chem Soc[J], 2009, 131,9886-9887.
[43] Kwak J, Kim M, Chang S, J Am Chem Soc[J], DOI:10.1021/ja111670s.
[29] Tan K L, Bergman R G, Ellman J A, J Am Chem Soc[J], 2001,123, 2685-2686.
[30] Wiedemann S H, Lewis J C, Ellman J A, etal. J Am Chem Soc[J], 2006, 128, 2452-2462.
[31] Li B–J,Yang S–D, Shi Z -J, Synlett[J],2008, 949-957.
[32] Tobisu M, Hyodo I, Chatani N, J Am Chem Soc[J], 2009,131,12070-12071.
[33] Geissman T A, Schlatter M J, Webb I D, etal. J Org Chem[J], 1946, 11, 741-750.
[34] Berman A M, Bergman R G, Ellman J A, J Org Chem[J], 2010,75,7863-7868.
[35] Gürbüz N, Ozdemir I, Cetinkaya B, Tetrahedron Lett. 2005, 46, 2273–2277.
[36] Lafrance M, Rowley C N, Woo T K, etal. J Am Chem Soc[J], 2006,128, 8754–8756.
[37] Lafrance M, Shore D, Fagnou K, Org Lett[J], 2006, 8, 5097–5100.
[38] Berman A M, Lewis J C, Bergman R G, J Am Chem Soc[J], 2008, 130, 14926-14927.s
[39] Nakao Y, Yamada Y, Kashihara N, J Am Chem Soc[J], 2010,132,13666-13668.
[40] Wasa M, Worrell B T, Yu J–Q, Angew Chem, Int Ed[J], 2010,49,1275-1277.
[41] Babu Y S, Rowland R S, Chand P, etal. US Patent No 6699994, 2004.
[42] Wasa M, Engle K M, Yu J -Q, J Am Chem Soc[J], 2009, 131,9886-9887.
[43] Kwak J, Kim M, Chang S, J Am Chem Soc[J], DOI:10.1021/ja111670s.
[1] Ghosh A K, Mathivanan P, Cappiello J, Tetrahedron: Asymmetry[J], 1998, 9, 1–45.
[2] J?rgensen K A, Johannsen M, Yao S, etal. Acc Chem Res[J],1999, 32, 605–613.
[3] Pfaltz A, Synlett[J], 1999,835–842; (d) Pfaltz A J, Heterocycl Chem[J], 1999, 36,1437–1451.
[4] Johnson J S, Evans D A , Acc Chem Res[J], 2000, 33, 325–335.
[5] Helmchen G., Pfaltz A, Acc Chem Res[J], 2000, 33, 336–345.
[6] Fache F, Schulz E, Tommasino M L, etal. Chem Rev. [J], 2000, 100, 2159–2231.
[7] Braunstein P, Naud F, Angew Chem, Int Ed[J], 2001, 40, 680–699.
[8] Rechavi D, Lemaire M, Chem Rev[J], 2002, 102, 3467–3493.
[9] Dai L X, Tu T, You S L, etal. Acc Chem Res[J], 2003,36, 659–667.
[10] Sutclie O B, Bryce M R, Tetrahedron: Asymmetry[J], 2003, 14, 2297–2325.
[11] Nishiyama H，Sakaguchi H, Nakamura T，etal.Organometallics[J], 1989, 8,846–848.
[12] Nishiyama H, Kondo M, NakamurT, etal. Organometallics[J], 1991, 10, 500–508.
[13] Nishiyama H, Yamaguchi S, Kondo M, etal. J Org Chem[J], 1992, 57, 4306–4309.
[14] Nishiyama H, Park S -B, Itoh K, Tetrahedron: Asymmetry[J], 1992, 3, 1029-1034.
[15] Nishiyama H, Itoh K, J Synth Org Chem Jpn[J], 1995, 53, 500–508.
[16] Nishiyama H, Itoh Y, Matsumoto H, etal. J Am Chem Soc[J], 1994, 116, 2223–2224.
[17] DBF-Box: Kanemasa S, Oderaotoshi Y, Wada E, J Am Chem Soc[J], 1999, 121,8675–8676.
[18] Iserloh U, Curran D P, Kanemasa S, Tetrahedron: Asymmetry[J],1999, 10, 2417–2428.
[19] Nakama K, Seki S, Kanemasa S, Tetrahedron Lett[J], 2002, 43, 829–832.
[20] Kanemasa S, Kanai T, J Am Chem Soc[J], 2000, 122, 10710–10711.
[21]Kanemasa S, Oderaotoshi Y, Sakaguchi S, etal. J Am Chem Soc[J], 1998, 120, 3074–3088.
[22] Kanemasa S, Oderaotoshi Y, Tanaka J, etal. Tetrahedron Lett[J], 1998, 39, 7521–7524.
[23] Voituriez A, Fiaud J–C, Schulz E, Tetrahedron Lett[J], 2002, 43, 4907–4909.
[24] Suzuki T, Kinoshita A, Kawada H, etal. Synlett[J], 2003, 570–572.
[25] Inoue M, Suzuki T, Nakada M, J Am Chem Soc[J], 2003, 125,1140–1141.
[26] Suzuki T, Kinoshita A, Kawada H, etal. Synlett[J], 2003, l570–572.
[27] Inoue M, Nakada M, Org Lett[J], 2004, 6, 2977–2980.
[28] Jiang Y, Jiang Q, Zhu G., etal. TetrahedronLett. [J], 1997, 38, 215–218.
[29] Jiang Y, Jiang Q, Zhang X, J Am Chem Soc[J], 1998, 120, 3817–3818.
[30] Glos M, ReiserO, Org Lett[J], 2000, 2, 2045–2048.
[31] TárragaA, Molina P, Curiel D, etal.Tetrahedron: Asymmetry[J], 2002, 13, 1621–1628.
[32] Abrunhosa I, Gulea M, Levillain J, etal.Tetrahedron: Asymmetry[J], 2001, 12, 2851–2859.
[33] Lafargue P, Guenot P, Lellouche J P, Synlett[J], 1995, 9, 171–172.
[34] Shibasaki M, Sasai H,Arai T,Angew Chem[J], 1997, 109, 1290–1310.
[25] Miyaura N, Suzuki A, Chem Rew[J],1995,95,2457-2483.
[36] Baudoin O, Gueritte f, Stud Nat Prod Chem[J],2003,29,355-417.
[37] Hayashi T, Hayashizaki K, Kiyoi t, etal.J Am Chem Soc[J],1988,10,8153-8156.
[38] Yin J, Buchwald S L, J Am Chem Soc[J], 2000,122,12051-12052.
[39] Cammidge A N, Crepy K V, Chem Commun[J], 2000,1723-1724.
[40] Herrbach A, Marinetti A, Baudoin O, etal. J Org Chem, 2003, 68,4897-4905.
[41] Lu S F, Du D M, Zhang S W, etal.Tetradron:Asymmetry[J], 2004,5,3433-3441.
[42] Zhang B S,Wang W, Shao D D,etal.Organometallics[J], DOI:10.1021/om100232n.
[2] Ritleng V, Sirlin C, Pfeffer M, Chem Rev[J], 2002, 102, 1731-1770.
[3] Tsuji J, Palladium Reagents and Catalysis: Innovations in Organic Synthesis, John Wiley,Chichester1995.
[4] Negishi E, de Meijere A Eds,Handbook of Organopalladium Chemistry for Organic Synthesis,John Wiley＆Sons , Inc: New York,2002;Vol.1-2.
[5] Tsuji J, Palladium Reagents and Catalysis: new Persspectives for the 21st Centry, 2nd ed. JohnWiley＆Son Ltd, 2004.
[6] Zaitsev V G., Shabashov D, Daugulis O, J Am Chem Soc[J], 2005,127, 13154-13155.
[7] Carey J S, Laffan D, Thomson C, etal. Org Biomol Chem[J], 2006, 4, 2337-2347.
[8] Campeau L–C, Rousseaux S, Fagnou K, J Am Chem Soc[J], 2005, 127, 18020-18021.
[9] Leclerc J–P, Fagnou K, Angew Chem Int Ed[J], 2006,45,7781-7786.
[10] Kanyiva K S, Nakao Y, Hiyama T, Angew Chem Int Ed[J], 2007,46,8872-8874.
[11] Campeau L–C, Schipper D J, Fagnou K, J Am Chem Soc[J], 2008, 130, 3266-3267.
[12] Zhao D, Wang W, Yang F, et al. Angew Chem Int Ed[J],2009,48,3296-3300.
[13] Campeau L–C, Stuart D R, Leclerc J–P, J Am Chem Soc[J], 2009, 131, 3291-3306.
[14] Huestis M P, Fagnou K, Org Lett[J], 2009,11,1357-1360.
[15] Schipper D J, El-Salfiti M, Whipp C J, etal. Tetrahedron[J], 2009,65,4977-4983.
[16] Larivée A, Mousseau J J, Charette A B, J Am Chem Soc[J],2008,130,52-54.
[17] Cho S H, Hwang S J, Chang S, J Am Chem Soc[J], 2008, 130, 9254-9256.
[18] Deng G ,Ueda K, Yanagisawa S, et al. Chem Eur J[J], 2009,15,333-337.
[19] Medley J W, Movassaghi M, J Org Chem[J], 2009,74,1341-1344.
[20] Wu J, Cui X, Chen L, etal. J Am Chem Soc[J], 2009,131,13888-13889.
[21] Patureau F W, Glorius F, Angew Chem Int Ed[J], 2011,50,1977-1979.
[22] Seiple I B, Su S, Rodriguez R A, etal. J Am Chem Soc[J],2010,132,13194-13196.
[23] Minisci F, Vismara E, Fontana F, Heterocycles[J], 1989, 28, 489-519.
[24] Godula K, Sezen B, Sames D, J Am Chem Soc[J], 2005,127,3648-3649.
[25] Nakao Y, Kanyiva K S, Hiyama T, J Am Chem Soc[J], 2008,130,2448-2449.
[26] Lewis J C, Bergman R T, Ellman J A, J Am Chem Soc[J], 2007,129,5332-5333.
[27] Tan K L, Bergman R G, Ellman J A , J Am Chem Soc[J], 2002,124, 3202-3203.
[28] Lewis J C, Wiedemann S H, Bergman R G, etal. Org Lett[J], 2004, 6, 35-38.
[29] Tan K L, Bergman R G, Ellman J A, J Am Chem Soc[J], 2001,123, 2685-2686.
[30] Wiedemann S H, Lewis J C, Ellman J A, etal. J Am Chem Soc[J], 2006, 128, 2452-2462.
[31] Li B–J,Yang S–D, Shi Z -J, Synlett[J],2008, 949-957.
[32] Tobisu M, Hyodo I, Chatani N, J Am Chem Soc[J], 2009,131,12070-12071.
[33] Geissman T A, Schlatter M J, Webb I D, etal. J Org Chem[J], 1946, 11, 741-750.
[34] Berman A M, Bergman R G, Ellman J A, J Org Chem[J], 2010,75,7863-7868.
[35] Gürbüz N, Ozdemir I, Cetinkaya B, Tetrahedron Lett. 2005, 46, 2273–2277.
[36] Lafrance M, Rowley C N, Woo T K, etal. J Am Chem Soc[J], 2006,128, 8754–8756.
[37] Lafrance M, Shore D, Fagnou K, Org Lett[J], 2006, 8, 5097–5100.
[38] Berman A M, Lewis J C, Bergman R G, J Am Chem Soc[J], 2008, 130, 14926-14927.s
[39] Nakao Y, Yamada Y, Kashihara N, J Am Chem Soc[J], 2010,132,13666-13668.
[40] Wasa M, Worrell B T, Yu J–Q, Angew Chem, Int Ed[J], 2010,49,1275-1277.
[41] Babu Y S, Rowland R S, Chand P, etal. US Patent No 6699994, 2004.
[42] Wasa M, Engle K M, Yu J -Q, J Am Chem Soc[J], 2009, 131,9886-9887.
[43] Kwak J, Kim M, Chang S, J Am Chem Soc[J], DOI:10.1021/ja111670s.
[29] Tan K L, Bergman R G, Ellman J A, J Am Chem Soc[J], 2001,123, 2685-2686.
[30] Wiedemann S H, Lewis J C, Ellman J A, etal. J Am Chem Soc[J], 2006, 128, 2452-2462.
[31] Li B–J,Yang S–D, Shi Z -J, Synlett[J],2008, 949-957.
[32] Tobisu M, Hyodo I, Chatani N, J Am Chem Soc[J], 2009,131,12070-12071.
[33] Geissman T A, Schlatter M J, Webb I D, etal. J Org Chem[J], 1946, 11, 741-750.
[34] Berman A M, Bergman R G, Ellman J A, J Org Chem[J], 2010,75,7863-7868.
[35] Gürbüz N, Ozdemir I, Cetinkaya B, Tetrahedron Lett. 2005, 46, 2273–2277.
[36] Lafrance M, Rowley C N, Woo T K, etal. J Am Chem Soc[J], 2006,128, 8754–8756.
[37] Lafrance M, Shore D, Fagnou K, Org Lett[J], 2006, 8, 5097–5100.
[38] Berman A M, Lewis J C, Bergman R G, J Am Chem Soc[J], 2008, 130, 14926-14927.s
[39] Nakao Y, Yamada Y, Kashihara N, J Am Chem Soc[J], 2010,132,13666-13668.
[40] Wasa M, Worrell B T, Yu J–Q, Angew Chem, Int Ed[J], 2010,49,1275-1277.
[41] Babu Y S, Rowland R S, Chand P, etal. US Patent No 6699994, 2004.
[42] Wasa M, Engle K M, Yu J -Q, J Am Chem Soc[J], 2009, 131,9886-9887.
[43] Kwak J, Kim M, Chang S, J Am Chem Soc[J], DOI:10.1021/ja111670s.
[1] Ghosh A K, Mathivanan P, Cappiello J, Tetrahedron: Asymmetry[J], 1998, 9, 1–45.
[2] J?rgensen K A, Johannsen M, Yao S, etal. Acc Chem Res[J],1999, 32, 605–613.
[3] Pfaltz A, Synlett[J], 1999,835–842; (d) Pfaltz A J, Heterocycl Chem[J], 1999, 36,1437–1451.
[4] Johnson J S, Evans D A , Acc Chem Res[J], 2000, 33, 325–335.
[5] Helmchen G., Pfaltz A, Acc Chem Res[J], 2000, 33, 336–345.
[6] Fache F, Schulz E, Tommasino M L, etal. Chem Rev. [J], 2000, 100, 2159–2231.
[7] Braunstein P, Naud F, Angew Chem, Int Ed[J], 2001, 40, 680–699.
[8] Rechavi D, Lemaire M, Chem Rev[J], 2002, 102, 3467–3493.
[9] Dai L X, Tu T, You S L, etal. Acc Chem Res[J], 2003,36, 659–667.
[10] Sutclie O B, Bryce M R, Tetrahedron: Asymmetry[J], 2003, 14, 2297–2325.
[11] Nishiyama H，Sakaguchi H, Nakamura T，etal.Organometallics[J], 1989, 8,846–848.
[12] Nishiyama H, Kondo M, NakamurT, etal. Organometallics[J], 1991, 10, 500–508.
[13] Nishiyama H, Yamaguchi S, Kondo M, etal. J Org Chem[J], 1992, 57, 4306–4309.
[14] Nishiyama H, Park S -B, Itoh K, Tetrahedron: Asymmetry[J], 1992, 3, 1029-1034.
[15] Nishiyama H, Itoh K, J Synth Org Chem Jpn[J], 1995, 53, 500–508.
[16] Nishiyama H, Itoh Y, Matsumoto H, etal. J Am Chem Soc[J], 1994, 116, 2223–2224.
[17] DBF-Box: Kanemasa S, Oderaotoshi Y, Wada E, J Am Chem Soc[J], 1999, 121,8675–8676.
[18] Iserloh U, Curran D P, Kanemasa S, Tetrahedron: Asymmetry[J],1999, 10, 2417–2428.
[19] Nakama K, Seki S, Kanemasa S, Tetrahedron Lett[J], 2002, 43, 829–832.
[20] Kanemasa S, Kanai T, J Am Chem Soc[J], 2000, 122, 10710–10711.
[21]Kanemasa S, Oderaotoshi Y, Sakaguchi S, etal. J Am Chem Soc[J], 1998, 120, 3074–3088.
[22] Kanemasa S, Oderaotoshi Y, Tanaka J, etal. Tetrahedron Lett[J], 1998, 39, 7521–7524.
[23] Voituriez A, Fiaud J–C, Schulz E, Tetrahedron Lett[J], 2002, 43, 4907–4909.
[24] Suzuki T, Kinoshita A, Kawada H, etal. Synlett[J], 2003, 570–572.
[25] Inoue M, Suzuki T, Nakada M, J Am Chem Soc[J], 2003, 125,1140–1141.
[26] Suzuki T, Kinoshita A, Kawada H, etal. Synlett[J], 2003, l570–572.
[27] Inoue M, Nakada M, Org Lett[J], 2004, 6, 2977–2980.
[28] Jiang Y, Jiang Q, Zhu G., etal. TetrahedronLett. [J], 1997, 38, 215–218.
[29] Jiang Y, Jiang Q, Zhang X, J Am Chem Soc[J], 1998, 120, 3817–3818.
[30] Glos M, ReiserO, Org Lett[J], 2000, 2, 2045–2048.
[31] TárragaA, Molina P, Curiel D, etal.Tetrahedron: Asymmetry[J], 2002, 13, 1621–1628.
[32] Abrunhosa I, Gulea M, Levillain J, etal.Tetrahedron: Asymmetry[J], 2001, 12, 2851–2859.
[33] Lafargue P, Guenot P, Lellouche J P, Synlett[J], 1995, 9, 171–172.
[34] Shibasaki M, Sasai H,Arai T,Angew Chem[J], 1997, 109, 1290–1310.
[25] Miyaura N, Suzuki A, Chem Rew[J],1995,95,2457-2483.
[36] Baudoin O, Gueritte f, Stud Nat Prod Chem[J],2003,29,355-417.
[37] Hayashi T, Hayashizaki K, Kiyoi t, etal.J Am Chem Soc[J],1988,10,8153-8156.
[38] Yin J, Buchwald S L, J Am Chem Soc[J], 2000,122,12051-12052.
[39] Cammidge A N, Crepy K V, Chem Commun[J], 2000,1723-1724.
[40] Herrbach A, Marinetti A, Baudoin O, etal. J Org Chem, 2003, 68,4897-4905.
[41] Lu S F, Du D M, Zhang S W, etal.Tetradron:Asymmetry[J], 2004,5,3433-3441.
[42] Zhang B S,Wang W, Shao D D,etal.Organometallics[J], DOI:10.1021/om100232n.