金属钯催化有机铝试剂与亲电试剂的偶联反应研究进展

doi:10.6023/cjoc201709041

摘要/Abstract

有机金属铝化合物因其活性高、中心金属铝的高Lewis酸性和较低的毒性而成为有机反应中优异的亲核试剂.因此，有机金属铝试剂广泛应用于交叉偶联反应中.主要对近年来金属钯催化的有机金属铝试剂在交叉偶联反应中的应用研究成果进行了综述，涉及各种反应体系.

关键词: 金属钯, 有机铝试剂, 偶联反应, 催化

Organoaluminum compounds are excellent nucleophiles for organic reactions because of their high reactivities, the high Lewis acidity of the aluminum center, and their low toxicities. Therefore, organoalanes are widely applied in cross-coupling reactions. In this paper, recent research results about the organoaluminum reagents applied in cross-coupling reactions catalyzed by palladium are reviewed, involving various reaction systems.

Key words: palladium, organoalanes, cross-coupling reaction, catalyze

引用此文

李清寒, 杓学蓓, 张刚, 丁勇, 杨学军, 陈峰. 金属钯催化有机铝试剂与亲电试剂的偶联反应研究进展[J]. 有机化学, 2018, 38(4): 802-811.

Li Qinghan, Shao Xuebei, Zhang Gang, Ding Yong, Yang Xuejun, Chen Feng. Recent Advance of Palladium-Catalyzed Cross-Coupling Reactions of Organoalanes with Electrophiles Reagents[J]. Chin. J. Org. Chem., 2018, 38(4): 802-811.

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参考文献

[1] (a) Tucker. C. E.; Vries, de J. G. Top. Catal. 2002, 19, 111.
(b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442.
(c) Johnson, J. B.; Rovis, T. Angew. Chem., Int. Ed. 2008, 47, 840.
(d) Torborg, C.; Beller, M. Adv. Synth. Catal. 2009, 351, 3027.
(e) Wu, X.-F.; Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 9047.
(f) Li, H.-B.; Johansson Seechurn, C. C. C.; Colacot, T. J. ACS Catal. 2012, 2, 1147.
(g) Sun, F.-Y.; Lv, L.-L.; Huang, M.; Zhou, Z.-H.; Fang, X.-D. Org. Lett. 2014, 16, 5024.
(h) Greco, R.; Goessler, W.; Cantillo, D.; Kappe, C. O. ACS Catal. 2015, 5, 1303.
(i) Ruiz-Castillo, P.; Buchwald, S. L. Chem. Rev. 2016, 116, 12564.
(j) Jedinak, L.; Zatopkova, R.; Zemankova, H.; Sustkova, A.; Cankar, P. J. Org. Chem. 2017, 82, 157.
(k) Liu, C.-W.; Liu, Y.-M.; Liu, R.-Z.; Lalancette, R.; Szostak, R.; Szostak, M. Org. Lett. 2017, 19, 1434.
(l) Halima, T. B.; Vandavasi, J. K.; Shkoor, M.; Newman, S. G. ACS Catal. 2017, 7, 2176.
[2] (a) Yu, D.-G.; Shi, Z.-J. Angew. Chem., Int. Ed. 2011, 50, 7079.
(b) Hirner, J. J.; Blum, S. A. Organometallics 2011, 30, 1299.
(c) Greene, M. A.; Yonova, I. M.; Williams, F. J.; Jarvo, E. R. Org. Lett. 2012, 14, 4293.
(d) Zhang, X.-Q.; Wang, Z.-X. Synlett 2013, 24, 2081.
(e) Everson, D. A.; Buonomo, J. A.; Weix, D. J. Synlett 2014, 25, 233.
(f) Li, Q.-H.; Ding, Y.; Yang, X. J. Chin. Chem. Lett. 2014, 25, 1296.
(g) Magano, J.; Monfette, S. ACS Catal. 2015, 5, 3120.
(h) Tarui, A.; Shinohara, S.; Sato, K.; Omote, M.; Ando, A. Org. Lett. 2016, 18, 1128.
(i) Li, Q.-H.; Ding, Y.; Zhang, G.; Zhang, Z.; Mo, S. Chin. J. Org. Chem. 2016, 36, 83(in Chinese). (李清寒, 丁勇, 张刚, 张震, 莫松, 有机化学, 2016, 36, 83.)
(j) Matsubara, K.; Yamamoto, H.; Miyazaki, S.; Inatomi, T.; Nonaka, K.; Koga, Y.; Yamada, Y.; Veiros, L. F.; Kirchner, K. Organometallics 2017, 36, 255.
[3] (a) Kang, S.-K.; Yamaguchi, T.; Kim, T.-H.; Ho, P.-S. J. Org. Chem. 1996, 61, 9082.
(b) Mao, Z.-F.; Wang, Z.; Xu, Z.-Q.; Huang, F.; Yu, Z.-K.; Wang, R. Org. Lett. 2012, 14, 3854.
(c) Hornillos, V.; Perez, M.; Fananas-Mastral, M.; Feringa, B. L. J. Am. Chem. Soc. 2013, 135, 2140.
(d) Santandrea, J.; Bedard, A. C.; Collins, S. K. Org. Lett. 2014, 16, 3892.
(e) Anima Bose, A.; Mal, P. J. Org. Chem. 2015, 80, 11219.
(f) Ding, S.-Y.; Xu, L.; Li, P.-F. ACS Catal. 2016, 6, 1329.
(g) Singh, S. K.; Chandna, N.; Jain, N. Org. Lett. 2017, 19, 1322.
(h) Sahoo, H.; Mukherjee, S.; Grandhi, G. S.; Selvakumar, J.; Baidya, M. J. Org. Chem. 2017, 82, 2764.
(i) Li, Q.-H.; Ding, Y.; Zhang, G.; Zhang, Z.; Mo, S. Curr. Org. Synth. 2017, 14, 462.
[4] (a) Baba, S.; Negishi, E.-I. J. Am. Chem. Soc. 1976, 98, 6729.
(b) Negishi, E-i.; Baba, S. J. Chem. Soc., Chem Commun. 1976, 596.
[5] (a) Negishi, E-i.; Zeng, X.; Tan, Z.; Qian, M.; Hu, Q.; Huang, Z. In Metal-catalyzed Cross-Coupling Reactions, Eds.:de Meijere, A.; Diederich, F., Vol. 2, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2004.
(b) Haas, D.; Hammann, J. M.; Greiner, R.; Knochel, P. ACS Catal. 2016, 6, 1540.
[6] (a) Andrus, M. B.; Meredith, E. L.; Hicken, E. J.; Simmons, B. L.; Glancey, R. R.; Ma, W. J. Org. Chem. 2003, 68, 8162.
(b) Liu, B.; Zhou, W.-S. Org. Lett. 2004, 6, 71.
(c) Elkhayat, Z.; Safir, I.; Dakir, M.; Arseniyadis, S. Tetrahedron Asymmetry 2007, 18, 1589.
(d) Chanu, A.; Safir, I.; Basak, R.; Chiaroni, A.; Arseniyadis, S. Org. Lett. 2007, 9, 1351.
[7] Woodward, S.; Dagorne, S. Topics in Organometallic Chemistry, Vol. 41, Springer, Berlin, 2013, pp. 1~322. For the synthesis of organoaluminum compounds, see pp. 173~186, in the chapter on Preparation of organoalanes for organic synthesis, by Knochel, P.; Blimke, T.; Groll, K.; Chen, Y.-H.; For cross-coupling reactions of organoaluminum compounds, see pp. 267~276, in chapter on Organoaluminum couplings to carbonyls, imines, and halides, by Kolb, A.; Zezschwitz, P.
[8] Hallwachs, W.; Schafarik, A. Justus Liebigs Ann. Chem. 1859, 109, 206.
[9] Maruoka, K.; Yamamoto, H. Tetrahedron 1988, 44, 5001.
[10] Wang, C.; Xi, Z. Chem. Soc. Rev. 2007, 36, 1395.
[11] Uhl, W. Coord. Chem. Rev. 2008, 252, 1540.
[12] (a) Mo, S.; Shao, X.-B.; Zhang, G.; Li, Q.-H. RSC Adv. 2017, 7, 27248.
(b) Zhang, Z.; Shao, X.-B.; Zhang, G.; Li, Q.-H.; Li, X.-Y. Synthesis 2017, 49, 3643.
(c) Zhang, Z.; Mo, S.; Zhang, G.; Shao, X.-B.; Li, Q.-H.; Zhong, Y. Synlett 2017, 28, 611.
[13] Blîmke, T.; Chen, Y. H.; Peng, Z.; Knochel, P. Nat. Chem. 2010, 2, 313.
[14] (a) Ohta, A.; Inoue, A.; Watanabe, T. Heterocycles 1984, 22, 2317.
(b) Ohta, A.; Inoue, A.; Ohtsuka, K.; Watanabe, T. Heterocycles 1985, 23, 133.
[15] Hirota, K.; Isobe, Y.; Maki, Y. J. Chem. Soc., Perkin Trans. 1 1989, 2513.
[16] Crisp, G. T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279.
[17] Hirota, K.; Kitade, Y.; Kanbe, Y.; Maki, Y. J. Org. Chem. 1992, 57, 5268.
[18] Mangalagiu, I.; Benneche, T.; Undheim, K. Tetrahedron Lett. 1996, 37, 1309.
[19] Blum, J.; Gelman, D.; Baidossi, W.; Shakh, E.; Rosenfeld, A.; Aizenshtat, Z.; Wassermann, B. C.; Frick, M.; Heymer, B.; Schutte, S.; Wernik, S.; Herbert, S. H. J. Org. Chem. 1997, 62, 8681.
[20] Biswas, K.; Chapron, A.; Cooper, T.; Fraser, P. K, Novak, A.; Prieto, O.; Woodward, S. Pure Appl. Chem. 2006, 78, 511.
[21] Vinogradov, A.; Woodward, S. Org. Synth. 2010, 87, 104.
[22] Cooper, T.; Novak, A.; Humphreys, L. D.; Walker, M. D.; Woodward, S. Adv. Synth. Catal. 2006, 348, 686.
[23] Conte, V.; Fiorani, G.; Floris, B.; Galloni, P.; Woodward, S. Appl. Catal. A:Gen. 2010, 381, 161.
[24] Baba, S.; Negishi, E.-I. J. Am. Chem. Soc. 1976, 98, 6729.
[25] Negishi, E-i.; Baba, S. J. Chem. Soc., Chem. Commun. 1976, 596.
[26] Negishi, E.-I.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. I. J. Am. Chem. Soc. 1978, 100, 2254.
[27] Zeng, F.; Negishi, E.-I. Org. Lett. 2001, 3, 719.
[28] Qian, M.; Huang, Z.; Negishi, E.-I. Org. Lett. 2004, 6, 1531.
[29] Chen, Q.-Y.; He, Y.-B. Chin. J. Chem. 1990, 8, 451.
[30] Zweifel, G.; Miller, R. L. Organic Reactions, Vol. 32, John Wileys, New York, 1984, p. 375.
[31] Samaritani, S.; Signore, G.; Malanga, C.; Menicagli, R. Tetrahedron 2005, 61, 14475.
[32] Andrews, P.; Latham, C. M.; Magre, M.; Willcox, D.; Woodward, S. Chem. Commun. 2013, 49, 1488.
[33] Fang, H.; Yang, Z.-Y.; Zhang, L.-J.; Wang, W.; Li, Y.-M.; Xu, X.-L.; Zhou, S.-L. Org. Lett. 2016, 18, 6022.
[34] Feuvrie, C.; Blanchet, J.; Bonin, M.; Micouin, L. Org. Lett. 2004, 6, 2333.
[35] Wang, B.; Bonin, M.; Micouin, L. Org. Lett. 2004, 6, 3481.
[36] Ku, S.-L.; Hui, X.-P.; Chen, C.-A.; Kuo, Y.-Y.; Gau, H.-M. Chem Commun. 2007, 3847.
[37] Shu, W.-T.; Zhou, S.-L.; Gau, H.-M. Synthesis 2009, 4075.
[38] Gao, H. J.; Knochel, P. Synlett 2009, 1321.
[39] Blümke, T.; Chen, Y.-H. Peng, Z.; Knochel, P. Nat. Chem. 2010, 2, 313.
[40] Groll, K.; Blümke, T. D.; Unsinn, A.; Haas, D.; Knochel, P. Angew. Chem., Int. Ed. 2012, 51, 11157.
[41] Chen, X.; Zhou, L.-M.; Li, Y.-M.; Xie, T.; Zhou, S.-L. J. Org. Chem. 2014, 79, 230.
[42] (a) Necas, D.; Kotora, M.; Clsarova, I. Eur. J. Org. Chem. 2004, 6, 1280.
(b) Necas, D.; Drabina, P.; Sedlak, M.; Kotora, M. Tetrahedron Lett. 2007, 48, 4539.
(c) Kawamura, S.; Ishizuka, K.; Takaya, H.; Nakamura, M. Chem. Commun. 2010, 46, 6054.
(d) Kawamura, S.; Kawabata, T.; Ishizuka, K.; Nakamura, M. Chem. Commun. 2012, 48, 9376.
[43] (a) Wunderlich, S. H.; Knochel, P. Angew. Chem., Int. Ed. 2009, 48, 1501.
(b) Blümke, T. D.; Groll, K.; Karaghiosoff, K.; Knochel, P. Org Lett. 2011, 13, 6440.
(c) Zhou, S.-L.; Yang, Z.-Y.; Chen, X.; Li, Y.-M.; Zhang, L.-J.; Fang, H.; Wang, W.; Zhu, X.-C.; Wang, S. W. J. Org. Chem. 2015, 80, 6323.
(d) Shrestha, B.; Thapa, S.; Gurung, S. K.; Pike, R. A. S.; Giri, R. J. Org. Chem. 2016, 81, 787.
[44] (a) Biradar, D. B.; Gau, H.-M. Chem. Commun. 2011, 47, 10467.
(b) Biradar, D. B.; Gau, H.-M. Org. Biomol. Chem. 2012, 10, 4243.
(c) He, F.; Wang, Z.-X. Tetrahedron 2017, 73, 4450.
(d) Mo, S.; Shao, X.-B.; Zhang, G.; Li, Q.-H. RSC Adv. 2017, 7, 27243.