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有机化学
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有机化学 ›› 2012, Vol. 32 ›› Issue (06): 986-993.DOI: 10.6023/cjoc1202082 上一篇    下一篇

综述与进展

铜催化含氮和硫化物的乙烯基化反应研究(特邀稿件)

廖骞, 席婵娟   

  1. 清华大学化学系 北京 100084
  • 收稿日期:2012-02-08 修回日期:2012-03-28 发布日期:2012-04-19
  • 通讯作者: 席婵娟 E-mail:cjxi@tsinghua.edu.cn

Investigation on Copper-catalyzed Vinylation of N- and S-centered Nucleophiles

Liao Qian, Xi Chanjuan   

  1. Department of Chemistry, Tsinghua University, Beijing 100084
  • Received:2012-02-08 Revised:2012-03-28 Published:2012-04-19

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以铜为催化剂,结合不同的反应条件,分别阐述了酰胺、胺、唑类化合物和硫化物与卤代烯烃的交叉偶联反应,从而分别得到了各种烯酰胺、烯胺、N-烯基唑类化合物和烯基硫醚化合物。上述亲核试剂与1,4-二卤-1,3-二烯化合物反应,经过两次乙烯基化反应,可以高效地得到各种取代的吡咯和噻吩衍生物。进一步阐述了N-H 键以及其邻位C-H 键也能够和1,4-二卤-1,3-二烯反应,生成唑并吡啶衍生物。

关键词: 铜催化, N-乙烯基化, S-乙烯基化, N-双乙烯基化, S-双乙烯基化

Copper could be catalyst on the alkenylation reactions of amides, amines, azoles and sulfides, which afforded efficient methods for the synthesis of alkenylamides, enamines, alkenylazoles and alkenylsulfides. Under the conditions of the coupling processes, it would be possible to effect a related transformation as a means to access heterocycles in one-pot. Accordingly, copper-catalyzed double alkenylations of amides, amines and sulfides to afford pyrroles and thiophenes have been expatiated. Furthermore, copper-catalyzed tandem alkenylations of azoles to afford nitrogen-bridgehead azolopyridine derivatives via an N-H bond and its adjacent C-H bond activation have been illustrated.

Key words: Copper-catalysis, N-vinylation, S-vinylation, N-double vinylation, S-double vinylation