有机硅试剂参与过渡金属催化的C—H官能团化反应形成C—C键的研究进展
收稿日期: 2014-10-09
修回日期: 2014-11-07
网络出版日期: 2014-12-02
基金资助
江西省教育厅自然科学基金(Nos. GJJ14668, KJLD14080)及江西省普通本科高校中青年教师发展计划访问学者专项资金资助项目.
Advance of Organosilane in Transition-Metal-Catalyzed C—H Functionalization for C—C Bond Formation
Received date: 2014-10-09
Revised date: 2014-11-07
Online published: 2014-12-02
Supported by
Project supported by the Natural Science Foundation of Jiangxi Provincial Education Department (Nos. GJJ14668, KJLD14080) and the Young Teacher Development Plan Visiting Scholar Special Funds of Jiangxi Ordinary Undergraduate Course Colleges and Universities.
作为一类重要的有机金属试剂, 有机硅试剂在有机合成化学的C—C键形成中得到了广泛应用. 综述了近年来有机硅试剂参与的过渡金属催化下C—H官能团化反应形成C—C键的研究进展, 重点介绍了Pd催化下C—H官能团化的Hiyama偶联反应.
关键词： 有机硅试剂; C—H官能团化; 过渡金属催化; C—C键形成; Hiyama偶联反应
罗海清 , 张志鹏 , 刘海东 , 柳辉金 . 有机硅试剂参与过渡金属催化的C—H官能团化反应形成C—C键的研究进展[J]. 有机化学, 2015 , 35(4) : 802 -812 . DOI: 10.6023/cjoc201410012
As a kind of important organometallic reagents, organosilanes have been widely applied for C—C bond formation in organic synthesis. In this paper, recent development of trans-metal-catalyzed C—H functionalizations for C—C bond formation involving organosilanes is reviewed, in which Pd-catalyzed Hiyama coupling reactions is described as highlighted.
[1] Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 3437.
[2] Kosugi, M.; Sasazawa, K.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301.
[3] Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320.
[4] (a) Chen, F.; Wang, T.; Jiao, N. Chem. Rev. 2014, 114, 8613.
(b) Liu, Z.-X.; Zhang, Y.; Wang, J.-B. Chin. J. Org. Chem. 2013, 33, 687 (in Chinese).
(刘振兴, 张艳, 王剑波, 有机化学, 2013, 33, 687.)
(c) Xu, W.; Sun, Y.-L.; Guo, M.-H.; Zhang, W.-Q.; Gao, Z.-W. Chin. J. Org. Chem. 2013, 33, 820 (in Chinese).
(徐伟, 孙原龙, 郭萌涵, 张伟强, 高子伟, 有机化学, 2013, 33, 820.)
(d) Chen, H.-L.; Li, S.-F.; Xu, J.-B.; Yang, Q.-J.; Zhou, Y.-Y.; Huang, C.; Fan, B.-M. Acta Chim. Sinica 2013, 71, 1243 (in Chinese).
(陈花磊, 李嗣锋, 徐建斌, 杨清镜, 刘珊珊, 周永云, 黄超, 樊保敏, 化学学报, 2013, 71, 1243.)
[5] Ackermann, L. Chem. Rev. 2011, 111, 1315.
[6] Wencel-Delord, J.; Droge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740.
[7] Zhang, S. Y.; Zhang, F. M.; Tu, Y. Q. Chem. Soc. Rev. 2011, 40, 1937.
[8] Giri, R.; Thapa, S.; Kafle, A. Adv. Synth. Catal. 2014, 356, 1395.
[9] (a) Dieck, H. A.; Heck. R. F. J. Org. Chem. 1975, 40, 1083.
(b) Kirchberg, S.; Frohlich, R.; Studer, A. Angew. Chem., Int. Ed. 2009, 48, 4235.
(c) Ge, H.; Niphakis, M. J.; Georg, G. I. J. Am. Chem. Soc. 2008, 130, 3708.
(d) Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634.
(e) Yang, J.; Deng, M.-Z.; Yu, T. Chin. J. Org. Chem. 2013, 33, 693 (in Chinese).
(杨军, 邓敏智, 于涛, 有机化学, 2013, 33, 693.)
[10] (a) Norinder, J.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 5858.
(b) Yoshikai, N.; Matsumoto, A.; Norinder, J.; Nakamura, E. Angew. Chem., Int. Ed. 2009, 48, 2925.
[11] Tobisu, M.; Hyodo, I.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 12070.
[12] (a) Nova, A.; Ujaque, G.; Maseras, F.; Lledos, A.; Espinet, P. J. Am. Chem. Soc. 2006, 128, 14571.
(b) Tobisu, M.; Hyodo, I.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 12070.
(c) Chen, X.; Li, J.-J.; Hao, X.-S.; Goohue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 78.
[13] Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821.
[14] Liang, Y. S.; Zhang, Z. Xi, J. Am. Chem. Soc. 2011, 133, 9204.
[15] Nakao, Y.; Hiyama, T. Chem. Soc. Rev. 2011, 40, 4893.
[16] Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918.
[17] Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918.
[18] Bi, L.; Georg, G. I. Org. Lett. 2011, 13, 5413.
[19] Denmark, S. E.; Butler, C. R. J. Am. Chem. Soc. 2008, 130, 3690.
[20] Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835.
[21] Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2004, 126, 4876.
[22] Hiyama, T.; Shirakawa, E. Top. Curr. Chem. 2002, 219, 61.
[23] Zhang, L.; Wu, J. J. Am. Chem. Soc. 2008, 130, 12250.
[24] Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527.
[25] Sezen, B.; Franz, R.; Sames, D. J. Am. Chem. Soc. 2002, 124, 13372.
[26] Zhang, B.; Guan, H.-X.; Shi, B.-F. Chin. J. Org. Chem. 2014, 34, 1487 (in Chinese).
(张博, 管晗曦, 刘斌, 史炳锋, 有机化学, 2014, 34, 1487.)
[27] Zaitsev, V. G.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 46.
[28] Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
[29] Tremont, S. J.; Rahman, H. U. J. Am. Chem. Soc. 1984, 106, 5759.
[30] Wan, X.; Ma, Z.; Li, B.; Zhang, K.; Cao, S.; Zhang, S.; Shi, Z. J. Am. Chem. Soc. 2006, 128, 7416.
[31] Yang, S.; Li, B.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 6066.
[32] Luo, H.-Q.; Dong, W. Synth. Commun. 2013, 43, 2733.
[33] Li, W.; Yin, Z.; Jiang, X.; Sun, P. J. Org. Chem. 2011, 76, 8543.
[34] Su, W. P.; Fan, H. X.; Shang, Y. P. Eur. J. Org. Chem. 2014, 16, 3323.
[35] Liang, Z.; Yao, B. B.; Zhang, Y. H. Org. Lett. 2010, 12, 3185.
[36] Ofial, R.; Han, W.; Mayer, P. Chem. Eur. J. 2011, 17, 6904.
[37] Bi, L.; Georg, G. Org. Lett. 2011, 13, 5413.
[38] Zhou, H.; Xu, Y. H.; Chung, W. J.; Loh, T. P. Angew. Chem., Int. Ed. 2009, 48, 5355.
[39] Tang, B.-X.; Fang, X.-N.; Kuang, R.-Y.; Zhou, X.-C. Chin. J. Org. Chem. 2013, 33, 319 (in Chinese).
(唐伯孝, 方小牛, 匡仁云, 周小春, 有机化学, 2013, 33, 319.)
[40] Ye, S. Z.; Liu, M. C.; Lin, B. D.; Wu, H. Y.; Ding, J. C.; Cheng, J. Tetrahedron Lett. 2009, 50, 530.
[41] Mori, A.; Danda, Y.; Fujii, T.; Hirabayashi, K.; Osakada, K. J. Am. Chem. Soc. 2001, 123, 74.
[42] Lu, M. Z.; Lu, P.; Xu, Y. H.; Luo, T. P. Org. Lett. 2014, 16, 2614.
[43] Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2010, 49, 2202.
[44] Koike, T.; Du, X.-L.; Sanada, T.; Danda, Y.; Mori, A. Angew. Chem., Int. Ed. 2003, 42, 89.
/
| 〈 |
|
〉 |
