Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (3): 610-617.DOI: 10.6023/cjoc201411017 Previous Articles     Next Articles

ARTICLE

铜催化炔基溴与丙炔醇的偶联-异构化反应合成戊炔烯酮(封面文章)

杨宗莲a, 廖沛球a, 李兴奇a, 毕锡和a,b   

  1. a 东北师范大学化学学院 长春 130024;
    b 南开大学元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2010-11-10 修回日期:2014-12-16 出版日期:2015-03-25 发布日期:2014-12-18
  • 通讯作者: 毕锡和 E-mail:bixh507@nenu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 21172029, 21202016, 21372038)资助项目.

Pentynenones Formation through Copper Catalyzed Coupling- Isomerization Reaction between Alkynyl Bromides and Propargylic Alcohols

Yang Zongliana, Liao Peiqiua, Li Xingqia, Bi Xihea,b   

  1. a Department of Chemistry, Northeast Normal University, Changchun 130024;
    b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071
  • Received:2010-11-10 Revised:2014-12-16 Online:2015-03-25 Published:2014-12-18
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21172029, 21202016, 21372038).

1,5-Disubstituted (E)-pent-2-en-4-yn-1-ones can be exclusively synthesized by copper-catalyzed tandem coupling-isomerization reaction of alkynyl bromides and secondary propargylic alcohols in piperidine. This method is operation-simple and allows the synthesis of a wide variety of stereodefined 1,5-disubstituted pentynenones in 40%~83% yields. The mechanistic investigations suggest that piperidine plays a duel role being both a solvent and a base in the reaction.

Key words: pentynenones, alkynyl bromides, propargylic alcohols, coupling-isomerization reaction