Progress in Phosphine-Promoted Annulations between Two Electrophiles

doi:10.6023/cjoc201406049

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (12): 2385-2405.DOI: 10.6023/cjoc201406049 Previous Articles Next Articles

REVIEW

叔膦促进下两种亲电试剂之间的环化反应研究进展

周荣^a, 刘蓉芳^a, 李瑞丰^a, 贺峥杰^b

a. 太原理工大学化学化工学院太原 030024;
b. 南开大学元素有机化学国家重点实验室天津化学化工协同创新中心天津 300071

收稿日期:2014-06-29 修回日期:2014-08-12 发布日期:2014-08-28
通讯作者: 周荣, 贺峥杰 E-mail:zhourong@tyut.edu.cn;zhengjiehe@nankai.edu.cn
基金资助:
国家自然科学基金(No.21272119)、太原理工大学引进人才基金(No.tyutrc-201357a)及太原理工大学青年基金(No.2013Z043)资助项目.

Progress in Phosphine-Promoted Annulations between Two Electrophiles

Zhou Rong^a, Liu Rongfang^a, Li Ruifeng^a, He Zhengjie^b

a. College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024;
b. State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071

Received:2014-06-29 Revised:2014-08-12 Published:2014-08-28
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21272119), the Qualified Personnel Foundation of Taiyuan University of Technology (No. tyutrc-201357a), and the Youth Foundation of Taiyuan University of Technology (No. 2013Z043).

The development of highly efficient synthetic methods of cyclic compounds is of great significance in the syntheses of pharmaceutically active molecules, natural products and other functional organic molecules. Recently, phosphine-promoted annulations of two electrophiles, which provide highly efficient access to various carbo-and heterocycles, have attracted extensive interest from synthetic chemists due to their merits such as ready availability of starting materials, mild and metal-free conditions. Generally, this kind of annulation reaction proceeds through a key step to generate an active zwitterionic intermediate via nucleophilic addition of the phosphine to an electrophile. According to different sources of the zwitterions, this review summarizes the recent progress in phosphine-promoted annulations of electron-deficient allenes, Morita-Baylis-Hillman allylic adducts, and electron-deficient alkenes with other electrophiles.

Key words: phosphine, electrophile, zwitterions, annulations

Cite this article

Zhou Rong, Liu Rongfang, Li Ruifeng, He Zhengjie. Progress in Phosphine-Promoted Annulations between Two Electrophiles[J]. Chin. J. Org. Chem., 2014, 34(12): 2385-2405.

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References

[1] Quin, L.D. A Guide to Organophosphorus Chemistry, Wiley, New York, 2000.
[2] (a) Wittig, G.; Schöllkopf, U. Chem. Ber. 1954, 87, 1318. (b) Mitsunobu, O. Synthesis 1981, 1. (c) Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635. (d) Xu, S.; He, Z. Chin. J. Org. Chem. 2012, 32, 1159 (in Chinese). (徐四龙, 贺峥杰, 有机化学, 2012, 32, 1159.)
[3] (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535. (b) Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 348, 1035. (c) Tang, Q.; Tu, A.; Deng, Z.; Hu, M.; Zhong, W. Chin. J. Org. Chem. 2013, 33, 954 (in Chinese). (唐谦, 涂爱平, 邓真真, 胡梦莹, 钟为慧, 有机化学, 2013, 33, 954.) (d) Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140. (e) Cowen, B. J.; Miller, S. J. Chem. Soc. Rev. 2009, 38, 3102. (f) Zhao, Q.-Y.; Lian, Z.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 1724. (g) Fan, Y. C.; Kwon, O. Chem. Commun. 2013, 49, 11588. (h) Wang, Z.; Xu, X.; Kwon, O. Chem. Soc. Rev. 2014, 43, 2927.
[4] Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906.
[5] (a) Xia, Y.; Liang, Y.; Chen, Y.; Wang, M.; Jiao, L.; Huang, F.; Liu, S.; Li, Y.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 3470. (b) Liang, Y.; Liu, S.; Xia, Y.; Li, Y.; Yu, Z.-X. Chem.-Eur. J. 2008, 14, 4361.
[6] (a) Mercier, E.; Fonovic, B.; Henry, C.; Kwon, O.; Dudding, T. Tetrahedron Lett. 2007, 48, 3617. (b) Dudding, T.; Kwon, O.; Mercier, E. Org. Lett. 2006, 8, 3643.
[7] (a) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031. (b) Xu, Z.; Lu, X. Tetrahedron Lett. 1999, 40, 549. (c) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461.
[8] Zhu, X.-F.; Henry, C. E.; Kwon, O. Tetrahedron 2005, 61, 6276.
[9] Zhang, B.; He, Z.; Xu, S.; Wu, G.; He, Z. Tetrahedron 2008, 64, 9471.
[10] (a) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477. (b) Yong, S. R.; Williams, M. C.; Pyne, S. G.; Ung, A. T.; Skelton, B. W.; White, A. H.; Turner, P. Tetrahedron 2005, 61, 8120.
[11] (a) Pham, T. Q.; Pyne, S. G.; Skelton, B. W.; White, A. H. J. Org. Chem. 2005, 70, 6369. (b) Wu, H.; Zhang, H.; Zhao, G. Tetrahedron 2007, 63, 6454. (c) Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463. (d) Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855. (e) Andrews, I. P.; Kwon, O. Chem. Sci. 2012, 3, 2510.
[12] Xu, S.; Zhou, L.; Ma, R.; Song, H.; He, Z. Chem. Eur. J. 2009, 15, 8698.
[13] Wang, T.; Ye, S. Org. Biomol. Chem. 2011, 9, 5260.
[14] Zhu, X.-F.; Lan, J.; Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716.
[15] (a) Tran, Y. S.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 12632. (b) Tran, Y. S.; Martin, T. J.; Kwon, O. Chem. Asian J. 2011, 6, 2101.
[16] (a) Villa, R. A.; Xu, Q.; Kwon, O. Org. Lett. 2012, 14, 4634. (b) Tran, Y. S.; Kwon, O. Org. Lett. 2005, 7, 4289.
[17] (a) Wurz, R. P.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 12234. (b) Zhong, F.; Han, X.; Wang, Y.; Lu, Y. Chem. Sci. 2012, 3, 1231. (c) Xiao, H.; Chai, Z.; Cao, D.; Wang, H.; Chen, J.; Zhao, G. Org. Biomol. Chem. 2012, 10, 3195.
[18] Wang, T.; Ye, S. Org. Lett. 2010, 12, 4168.
[19] Li, E.; Huang, Y.; Liang, L.; Xie, P. Org. Lett. 2013, 15, 3138.
[20] Gicquel, M.; Gomez, C.; Retailleau, P.; Voituriez, A.; Marinetti, A. Org. Lett. 2013, 15, 4002.
[21] (a) Meng, X. T.; Huang, Y.; Chen, R. Y. Org. Lett. 2009, 11, 137. (b) Sun, Y.-W.; Guan, X.-Y.; Shi, M. Org. Lett. 2010, 12, 5664. (c) Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023. (d) Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787. (e) Liu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595. (f) Zhu, X. F.; Henry, C. E.; Wang, J.; Dudding, T.; Kwon, O. Org. Lett. 2005, 7, 1387. (g) Zhu, X.-F.; Schaffner, A.-P.; Li, R. C.; Kwon, O. Org. Lett. 2005, 7, 2977. (h) Creech, G. S.; Kwon, O. Org. Lett. 2008, 10, 429. (i) Jing, C,; Na, R.; Wang, B.; Liu, H.; Zhang, L.; Liu, J.; Wang, M.; Zhong, J.; Kwon, O.; Guo, H. Adv. Synth. Catal. 2012, 354, 1023. (j) Zheng, J.; Huang, Y.; Li, Z. Org. Lett. 2013, 15, 5064. (k) Li, E.; Jia, P.; Liang, L.; Huang, Y. ACS Catal. 2014, 4, 600. (l) Li, E.; Huang, Y. Chem. Commun. 2014, 50, 948. (m) Li, E.; Huang, Y. Chem. Eur. J. 2014, 20, 3520.
[22] Guo, H.; Xu, Q.; Kwon, O. J. Am. Chem. Soc. 2009, 131, 6318.
[23] Na, R.; Jing, C.; Xu, Q.; Jiang, H.; Wu, X.; Shi, J.; Zhong, J.; Wang, M.; Benitez, D.; Tkatchouk, E.; Goddard, W. A.; Guo, H.; Kwon, O. J. Am. Chem. Soc. 2011, 133, 13337.
[24] Du, Y.; Lu, X.; Zhang, C. Angew. Chem., Int. Ed. 2003, 42, 1035.
[25] Feng, J.; Lu, X.; Kong, A.; Han, X. Tetrahedron 2007, 63, 6035.
[26] Zheng, S.; Lu, X. Tetrahedron Lett. 2009, 50, 4532.
[27] Deng, H.-P.; Wei, Y.; Shi, M. Org. Lett. 2011, 13, 3348.
[28] Zhong, F.; Han, X.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2011, 50, 7837.
[29] Tan, B.; Candeias, N. R.; Barbas, C. F. J. Am. Chem. Soc. 2011, 133, 4672.
[30] Zhong, F.; Chen, G.-Y.; Han, X.; Yao, W.; Lu, Y. Org. Lett. 2012, 14, 3764.
[31] Zheng, S.; Lu, X. Org. Lett. 2008, 10, 4481.
[32] Du, Y.; Feng, J.; Lu, X. Org. Lett. 2005, 7, 1987.
[33] Zheng, S.; Lu, X. Org. Lett. 2009, 11, 3978.
[34] Zhou, R.; Wang, J.; Song, H.; He, Z. Org. Lett. 2011, 13, 580.
[35] Chen, Z.; Zhang, J. Chem. Asian J. 2010, 5, 1542.
[36] Tian, J.; Zhou, R.; Sun, H.; Song, H.; He, Z. J. Org. Chem. 2011, 76, 2374.
[37] Zhou, R.; Duan, C.; Yang, C.; He, Z. Chem. Asian. J. 2014, 9, 1183.
[38] Xie, P.; Huang, Y.; Chen, R. Org. Lett. 2010, 12, 3768.
[39] (a) Zhang, X.; Deng, H.-P.; Huang, L.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 8664. (b) Hu, F.-L.; Wei, Y.; Shi, M. Chem. Commun. 2014, 50, 8912.
[40] Xie, P.; Huang, Y.; Chen, R. Chem. Eur. J. 2012, 18, 7362.
[41] Xie, P.; Li, E.; Zheng, J.; Li, X.; Huang, Y.; Chen, R. Adv. Synth. Catal. 2013, 355, 161.
[42] Zheng, J.; Huang, Y.; Li, Z. Chem. Commun. 2014, 50, 5710.
[43] Aroyan, C. E.; Dermenci, A.; Miller, S. J. Tetrahedron 2009, 65, 4069.
[44] (a) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811. (b) Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447. (c) Cui, P.-L.; Wang, C.; Guo, X.-M.; Liu, H.-Y.; Feng, T. Chin. J. Org. Chem. 2008, 28, 194 (in Chinese). (崔朋雷, 王春, 果秀敏, 刘海燕, 冯涛, 有机化学, 2008, 28, 194.)
[45] Cai, L.; Zhang, B.; Wu, G.; Song, H.; He, Z. Chem. Commun. 2011, 47, 1045.
[46] Zhou, R.; Wang, J.; Tian, J.; He, Z. Org. Biomol. Chem. 2012, 10, 773.
[47] Hu, F.-L.; Wei, Y.; Shi, M. Adv. Synth. Catal. 2014, 356, 736.
[48] Zhou, R.; Wang, J.; Yu, J.; He, Z. J. Org. Chem. 2013, 78, 10596.
[49] Ma, J.; Xie, P.; Hu, C.; Huang, Y.; Chen, R. Chem. Eur. J. 2011, 17, 7418.
[50] Schuler, M.; Duvvuru, D.; Retailleau, P.; Betzer, J.-F.; Marinetti, A. Org. Lett. 2009, 11, 4406.
[51] Shi, Z.; Tong, Q.; Leong, W. W. Y.; Zhong, G. Chem. Eur. J. 2012, 18, 9802.
[52] Shi, Z.; Yu, P.; Loh, T.-P.; Zhong, G. Angew. Chem., Int. Ed. 2012, 51, 7825.
[53] (a) Zhang, X.-N.; Chen, G.-Q.; Dong, X.; Wei, Y.; Shi, M. Adv. Synth. Catal. 2013, 355, 3351. (b) Zhang, X.-N.; Dong, X.; Wei, Y.; Shi, M. Tetrahedron 2014, 70, 2838.
[54] Kao, T.-T.; Syu, S.; Jhang, Y.-W.; Lin, W. Org. Lett. 2010, 12, 3066.
[55] Lee, C.-J.; Jang, Y.-J.; Wu, Z.-Z.; Lin, W. Org. Lett. 2012, 14, 1906.
[56] Chen. K.-W.; Syu, S.; Jang, Y.-J.; Lin, W. Org. Biomol. Chem. 2011, 9, 2098.
[57] Syu. S.; Lee, Y.-T.; Jang, Y.-J.; Lin, W. Org. Lett. 2011, 13, 2970.
[58] Wang, J.; Zhou, R.; He, Z.-R.; He, Z. Eur. J. Org. Chem. 2012, 6033.

叔膦促进下两种亲电试剂之间的环化反应研究进展

Progress in Phosphine-Promoted Annulations between Two Electrophiles

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