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2012 , Vol. 32 >Issue 06: 994 - 1009

DOI: https://doi.org/10.6023/cjoc1202073

综述与进展

炔烃偶联反应研究的新进展（特邀稿件）

  • 白东虎 ,
  • 李春举 ,
  • 李健 ,
  • 贾学顺
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  • a 上海大学化学系 上海 200444;
    b 中国科学院上海有机化学研究所天然产物有机合成化学重点实验室 上海 200032

收稿日期: 2012-02-07

  修回日期: 2012-03-26

  网络出版日期: 2012-04-10

基金资助

国家自然科学基金（21142012, 21002061, 20902057）和中国科学院上海有机化学研究所天然产物有机合成化学重点实验室基金支持

收起

New Progress of Acetylene-Coupling Reactions

  • Bai Donghu ,
  • Li Chunju ,
  • Li Jian ,
  • Jia Xueshun
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  • a Department of Chemistry, Shanghai University, Shanghai, 200444, China;
    b Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China

Received date: 2012-02-07

  Revised date: 2012-03-26

  Online published: 2012-04-10

Supported by

Project supported by the the National Natural Science Foundation of China (No: 21142012, 21002061, 20902057), the Key Laboratory of Synthetic Chemistry of Natural Substances, Chinese Academy of Sciences.

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摘要

综述了近几年来炔偶联反应的新进展,主要涉及铜试剂和钯试剂催化的端炔偶联反应以及反应机理和应用。

关键词： 炔; 炔偶联; 铜催化; 钯催化; 反应

本文引用格式

白东虎 , 李春举 , 李健 , 贾学顺 . 炔烃偶联反应研究的新进展（特邀稿件）[J]. 有机化学, 2012 , 32(06) : 994 -1009 . DOI: 10.6023/cjoc1202073

Abstract

The recent studies of acetylene-coupling reactions are reviewed, mainly focusing on copper reagents and palladium reagents catalyzed coupling reactions of terminal alkyne as well as the reaction mechanism and application.

Key words： alkyne; alkyne coupling; copper catalysis; palladium catalysis; reaction

参考文献

[1] (a) Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2, 422. (b) Glaser, C. Ann. Chem. Pharm. 1870, 154, 137.  

[2] Annabelle, L. K.; Shun, S.; Tykwinski, R. Angew. Chem. Int. Ed. 2006, 45, 1034.  

[3] Xu, Z. F.; Kaha, M.; Walker, K. L. J. Am. Chem. Soc. 1994,116, 4537.  

[4] (a) Sienmsen, P.; Livingston, R. C.; Diederich,F. Angew. Chem. Int. Ed. 2000, 39, 2632. (b) Stefani, H. A.; Guarezemini, A. S.; Cella, R. Tetrahedron 2010, 66, 7871.  

[5] Tang, J. Y.; Jiang, H. F.; Deng, G. H.; Zhou. L. Chin. J. Org. Chem. 2005, 25,1503.

[6] Eglinton, G.; Galbraith, A. R. Chem. Ind. (London) 1956, 737.

[7] K黵ti, L.; Czak?, B. Strategic Applications of Named Reactions in Organic Synthesis.2007,p.186.

[8] Hay, A. S. J. Org. Chem. 1962, 27, 3320.  

[9] Yadav, J. S.; Reddy, B. V. S.; Bhaskar Reddy, K.; Gayathri, U. K.; Prasad, A. R. Tetrahedron Lett. 2003, 44, 6493.  

[10] Ranu, B. C.; Banerjee, S. Lett. Org. Chem. 2006, 3, 607.  

[11] Ye, C.; Xiao, J.; Twamley, B. Shreeve, J. M. Eur. J. Org. Chem. 2007, 5095.  

[12] (a) Li, J.; Jiang, H. Chem. Commun. 1999, 2369. (b) Jiang, H.; Tang, J.; Wang, A.; Deng, G.; Yang, S. Synthesis 2006, 1155.  

[13] (a) Kuhn, P.; Sommer, J. Eur. J. Org. Chem. 2009, 423. (b) Kuhn, P.; Pale, P.; Sommer, J.; Louis,B. J. Phys. Chem. C 2009, 113, 2903.  

[14] Alix, A.; Pale, P. Synthesis 2010, 1557.  

[15] Wang, D.; Li, J.; Gao, T.; Hou, S.; Chen, B. Green Chem. 2010, 12, 45.  

[16] (a) Yin, K.; Li, C.; Li, J.; Jia, X. Green Chem. 2011, 13, 591. (b) Yin, K.; Li, C.; Li, J.; Jia, X. Appl. Organometal. Chem. 2011, 25, 16. (c) Li, D.; Yin, K.; Li, J.; Jia, X. Tetrahedron Lett. 2008, 49, 5918. (d) Jia, X.; Yin, K.; Li, C.; Li, J.; Bian, H. Green Chem. 2011, 13, 2175.  

[17] Schmidt, R.; Thorwirth, R.; Szuppa, T.; Stolle, A.; Ondruschka, B.; Hopf, H. Chem. Eur. J. 2011, 17, 8129.

[18] Oishi, T.; Yamaguchi, K.; Mizuno, N. ACS Catal. 2011, 1, 1351.  

[19] Wu, T.; Huang, S.; Tsai, F. Appl. Organometal. Chem. 2011, 25, 395.  

[20] Zhang, S.; Liu, X.; Wang, T. Adv. Synth. Catal. 2011, 353, 1463.  

[21] Zhu, B. C.; Jiang, X. Z. Appl. Organometal. Chem. 2007, 21, 345.  

[22] Nador, F.; Fortunato, L.; Moglie, Y.; Vitale, C.; Radivoy, G. Synthesis 2009, 4027.

[23] Alonso, F.; Melkonian, T. Moglie, Y.; Yus, M. Eur. J. Org. Chem. 2011, 2524.

[24] Oishi, T.; Katayama, T.; Yamaguchi, K.; Mizuno, N. Chem. Eur. J. 2009, 15, 7539.  

[25] Balamurugan, R.; Naveen, N.; Manojveer, S.; Nama, M. V. Aust. J. Chem. 2011, 64, 567.

[26] Balaraman, K.; Kesavan, V. Synthesis 2010, 3461.  

[27] Kusuda, A.; Xu, X. H.; Wang, X.; Tokunaga, E.; Shibata, N. Green Chem. 2011, 13, 843.  

[28] Rossi, R.; Carpita, A.; Bigelli, C. Tetrahedron Lett. 1985, 26, 523.  

[29] (a) Liu, Q.; Burton, D. J. Tetrahedron Lett. 1997, 38, 4371. (b)Hattori,T.; Kijima,M.; Shirakawa,H. Synth.Met.1997,84,357.  

[30] Alonso,D. A.; Najera, C.; Pacheco, M. Adv. Synth. Catal. 2003, 345, 1146.  

[31] Gil-Molt?, J.; Najer?, C. Eur. J. Org. Chem. 2005, 4073.

[32] Lei, Z.; Ying, Z.; Ling, L.; Feng, J. Chin. J. Chem. 2007, 25, 1413.

[33] Kurita, T.; Abe, M.; Maegawa, T.; Monguchi, Y.; Sajiki, H. Synlett 2007, 2521.

[34] Watarai, N.; Kawasaki, H.; Saito, S. Heterocycles, 2009, 79, 531.  

[35] Perrone, S.; Bona, F.; Troisi, L. Tetrahedron 2011, 67, 7386.  

[36] Li, J. X.; Liang, H. R.; Wang, Z. Y.; Fu, J. H. Monatsh. Chem. 2011, 142, 507.  

[37] Bharathi, P.; Periasamy, M. Organometallics 2000, 19, 5511.  

[38] Krafft,M. E.; Hirosawa, C. Dalal, N.; Ramsey, C.; Stiegman, A. Tetrahedron Lett. 2001, 42, 7733.  

[39] Hilt, G.; Hengst, C.; Arndt, M. Synthesis 2009, 395.

[40] Yin, W.; He, C.; Chen, M.; Zhang, H.; Lei, A. Org. Lett. 2009, 11, 709.  

[41] Peng, J.; Liu, X.; Kishi, Y. Tetrahedron Lett. 2011, 52, 2172.  

[42] (a) Yamaguchi, K.; Kamata, K.; Mizuno, N. J. Catal. 2008, 258, 121. (b) Mizuno, N.; Yamaguchi, K.; Kamata, K. Catal. Surv. Asia. 2011, 15, 68.  

[43] (a) Chodkiewicz, W.; Cadiot, P.; Hebd, C.R. Hebd. Seances Acad. Sci. 1955, 241, 1055. (b) Chodkiewicz, W. Ann. Chim. (paris) 1957, 2, 819.

[44] Shen, W.; Thomas, S. A. Org. Lett. 2000, 2, 18, 2857.

[45] Shi, W.; Luo, Y.; Luo, X.; Lei, A. J. Am. Chem. Soc. 2008, 130, 14713.  

[46] Damle, S.; Seomoon, D.; Lee, P. H. J. Org. Chem. 2003, 68, 7085.  

[47] Xue, S.; Meng, L.; Guo, Q.; Synth. Commun. 2008, 38, 2243.  

[48] Chen, Z.; Jiang, H.; Wang, A.; Yang, S. J. Org. Chem. 2010, 75, 6700.  

[49] Cahiez, G.; Duplais, C.; Buendia, J. Angew. Chem. Int. Ed. 2009, 48, 6731.  

[50] Kude, K.; Hayase, S.; Kawatsura, M. Itoh, T. Heteroatom Chem. 2011, 22, 398.

[51] Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.  

[52] Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Chem. Commun. 2003, 1510.

[53] Oh, C. H.; Reddy, V. R. Tetrahedron Lett. 2004, 45, 5221.  

[54] Nishihara, Y.; Okamoto, M.; Inoue, Y. Tetrahedron Lett. 2005, 46, 8661.  

[55] Shirakawa, E.; Nakao, Y.; Murota, Y.; Hiyama, T. J. Organomet. Chem. 2003, 670, 132.  

[56] Ochiai, M.; Nishi, Y.; Goto, S.; Frohn, H. J. Angew. Chem. Int. Ed. 2005, 44, 406.  

[57] Singh, F. V.; Amaral, M.; Stefani, H. A. Tetrahedron Lett. 2009, 50, 2636.  

[58] (a) Zalkind, Y. S.; Fundyler, F. B. Ber. Chem. Ges. 1936, 69, 128. (b) Zalkind, Y. S.; Fundyler, F. B. J. Gen. Chem. USSR 1939, 9, 1725.

[59] Clifford, A. A.; Water, W. A. J. Chem. Soc. 1963, 3056.

[60] Bohlmann, F. Schonowsky, H.; Inhoffen, E.; Grau, G. Chem. Ber. 1964, 97, 794.  

[61] Alper, H.; Maldonado, M. Organometallics 1989, 8, 1124.  

[62] Liu, Q.; Burton, D. J. Tetrahedron Lett. 1997, 38, 4371.  

[63] Bumagin, N. A.; Ponomarev, A. B.; Beletskaya, I. P. B.Acad.Sci. USSR 1984, 33, 1433.  

[64] Cai, C.; Vasella, A. Helv. Chim. Acta. 1995, 78, 2053.  

[65] Mohr, W.; Stahl, J.; Hampel, F.; Gladysz, J. A. Chem. Eur. J. 2003, 9, 3324.

[66] (a) Zhou, N.; Zhao, Y. J. Org. Chem. 2010, 75, 1498. (b) Chen, G.; Mahmud,I.; Dawe, L. N.; Zhao, Y. J. Org. Chem. 2011, 76, 2701.  

[67] Lee, J. W.; Han, S. C.; Lee, U.; Kim, B.; Kim, J.H. Bull. Korean Chem. Soc. 2009, 30, 1925.  

[68] Campbell, K.; Tiemstra, N. M.; Tykwinski, R. Synlett 2004, 182.  

[69] Takeda, T.; Fix, A. G.; Haley, M. Org. Lett. 2010, 12, 3824.  

[70] Prasad, K. R.; Swain, B. Tetrahedron: Asymmetry 2011, 22, 1261.  

[71] Takamura, H.; Wada, H.; Lu, Nan.; Kadota, I. Org. Lett. 2011, 13, 3644.

[72] (a) Berna, J.; Goldup, S. M.; Lee, A. L.; Leigh, D. A.; Zerbetto, F. Angew. Chem. Int. Ed. 2008, 47, 4392. (b) Goldup, S. M.; Leigh, D. A.; Long, T.; McGonigal, P. R.; Symes, M. D.; Wu, J. J. Am. Chem. Soc. 2009, 131, 15924. (c) Crowley, J. D.; Goldup, S. M.; Gowans, N. D.; Leigh, D. A. J. Am. Chem. Soc. 2010, 132, 6243.  

[73] Saito, S.; Takahashi, E.; Nakazono, K. Org. Lett. 2006, 8, 5133.  

[74] Langton, M. J.; Matichak, J. D.; Thompson, A. L.; Anderson, H. L. Chem. Sci. 2011, 2, 1897.  

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