金催化2-炔基芳基叠氮串联反应有效合成3-炔基吲哚
收稿日期: 2015-01-30
修回日期: 2015-03-23
网络出版日期: 2015-03-24
基金资助
国家自然科学青年基金(No. 21302096)、江苏省自然科学青年基金(No. BK20130962)和江苏高校优势学科建设工程(PAPD)资助项目.
Gold-Catalyzed Tandem Reactions of 2-Alkynyl Arylazides: Efficient Access to 3-Alkynyl Indoles
Received date: 2015-01-30
Revised date: 2015-03-23
Online published: 2015-03-24
Supported by
Project supported by the Young National Natural Science Foundation of China (No. 21302096), the Young Natural Science Foundation of Jiangsu Province (No. BK20130962) and the Project Fund from the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).
张小祥 , 孙小萍 , 崔杏丽 , 张海飞 . 金催化2-炔基芳基叠氮串联反应有效合成3-炔基吲哚[J]. 有机化学, 2015 , 35(8) : 1700 -1706 . DOI: 10.6023/cjoc201501045
3-Alkynyl indoles were efficiently prepared through trapping of α-imine gold carbenes by alkynes, generated by gold-catalyzed tandem reactions of 2-alkynyl arylazides. The desired products were afforded up to 94% yield at 60 ℃ with 2 mol% JohnPhosAuCl as catalyst. A very simple and general synthetic method for the efficient synthesis of 3-alkynyl indoles was provided.
Key words： α-imino gold carbene; tandem reaction; alkyne; 3-alkynyl indole
[1] (a) Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489. (b) McKay, M. J.; Carroll, A. R.; Quinn, R. J.; Hooper, J. N. A. J. Nat. Prod. 2002, 65, 595.
[2] Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172.
[3] (a) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873. (b) Seregin, I. V.; Ryabova, V.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 7742. For recent examples of Pd-catalyzed arylation of indoles, see: (c) Lane, B. S.; Sames, D. Org. Lett. 2004, 6, 2897. (d) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050. (e) Bressy, C.; Alberico, D.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 13148. (f) Deprez, N. R.; Kalyani, D.; Krause, A.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972. (g) Wang, X.; Gribkov, D. V.; Sames, D. J. Org. Chem. 2007, 72, 1476. (h) Dwight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. Org. Lett. 2007, 9, 3137. (i) Stuart, D. R.; Villemure, E.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 12072. For recent examples of Pd-catalyzed vinylation of indoles, see: (j) Jia, C.; Lu, W.; Kitamura, T.; Fujiwara, Y. Org. Lett. 1999, 1, 2097. (k) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 95783. (l) Liu, C.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 10250. (m) Grimster, N. P.; Gauntlett, C.; Godfrey, C. R. A.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3125. (n) Zhang, D.; Qin, Y. Acta Chim. Sinica. 2013, 71, 147 (in Chinese). (张丹, 秦勇, 化学学报, 2013, 71, 147.) (o) Li, S.; Han, J.; Li, A. Acta Chim. Sinica 2013, 71, 295 (in Chinese). (李森, 韩静, 李昂, 化学学报, 2013, 71, 295.) (p) Xie, W.-Q.; Zuo, Z.-W.; Zi, W.-W.; Ma, D.-W. Chin. J. Org. Chem. 2013, 33, 869 (in Chinese). (谢卫青, 左智伟, 资伟伟, 马大为, 有机化学, 2013, 33, 869.) (q) Dan, D.; Jia, Y.-X. Chin. J. Org. Chem. 2013, 33, 1144 (in Chinese). (单冬, 贾彦兴, 有机化学, 2013, 33, 1144.) (r) Liu, Y.-L.; Zhu, F.; Wang, C.-H.; Zhou, J. Chin. J. Org. Chem. 2013, 33, 1595 (in Chinese). (刘运林, 朱锋, 王翠红, 周剑, 有机化学, 2013, 33, 1595.)
[4] (a) Yue, D.; Larock, R. C. Org. Lett. 2004, 6, 1037. (b) Zhang, H.; Larock, R. C. J. Org. Chem. 2002, 67, 7048. (c) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. J. Org. Chem. 2005, 70, 6213. (d) Gu, Y.; Wang, X.-M. Tetrahedron Lett. 2009, 50, 763.
[5] For selected reviews on gold catalysis, see: (a) Hashmi, A. S. K. Acc. Chem. Res. 2014, 47, 864. (b) Yeom, H.-S.; Shin, S. Acc. Chem. Res. 2014, 47, 966. (c) Zhang, L. Acc. Chem. Res. 2014, 47, 877. (d) Zhang, S.; Wei, F.; Song, C.; Jia, J.; Xu, Z. Chin. J. Chem. 2014, 32, 937. (e) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084. (f) Zhang, Y.; Luo, S.; Zhu, C. Chin. J. Org. Chem. 2012, 32, 2073 (in Chinese). (张艳, 罗莎, 朱成建, 有机化学, 2012, 32, 2073.) (g) Luo, P.; Tang, R.; Zhong, P.; Li, J. Chin. J. Org. Chem. 2009, 29, 1924 (in Chinese). (罗培松, 汤日元, 钟平, 李金恒, 有机化学, 2009, 29, 1924.) (h) Obradors, C.; Echavarren, A. M. Acc. Chem. Res. 2014, 47, 902. (i) Furstner, A. Chem. Soc. Rev. 2009, 38, 3208. (j) Arcadi, A. Chem. Rev. 2008, 108, 3266. (k) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351. (l) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180. (m) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395. (n) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239. (o) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084.
[6] (a) Zhang, X.-X.; Sun, X.-P.; Zhang, H.-F.; Cui, X.-L.; Ma, M.-T. Chin. J. Org. Chem. 2015, 35, 1469 (in Chinese). (张小祥, 孙小萍, 张海飞, 崔杏丽, 马猛涛, 有机化学, 2015, 35, 1469.) (b) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260. (c) Witham, C. A.; Mauleon, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838.
[7] (a) Gronnier, C.; Boissonnat, G.; Gagosz, F. Org. Lett. 2013, 15, 4234. (b) Yan, Z.; Xiao, Y.; Zhang, L. Angew. Chem., Int. Ed. 2012, 51, 8624. (c) Xiao, Y.; Zhang, L. Org. Lett. 2012, 14, 4662. (d) Witham, C. A.; Mauleon, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838. (e) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
[8] Lu, B.; Luo, Y.; Liu, L.; Ye, L.; Wang, Y.; Zhang, L. Angew. Chem., Int. Ed. 2011, 50, 8358.
[9] Wetzel, A.; Gagosz, F. Angew. Chem., Int. Ed. 2011, 50, 7354.
[10] Li, N.; Wang, T.-Y.; Gong, L.-Z.; Zhang, L. Chem. Eur. J. 2015, 21, 1.
[11] Zhao, L.; Wang, J.; Zhang, H.; Li, Y.; Yang, K.; Cheng, B.; Jin, X.; Yao, Y.; Zhai, H. Org. Lett. 2014, 16, 6378.
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