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

doi:10.6023/cjoc201411017

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

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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

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 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 Zonglian^a, Liao Peiqiu^a, Li Xingqi^a, Bi Xihe^a,b

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 Published:2014-12-18
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21172029, 21202016, 21372038).

1. Pentynenones Formation through Copper Catalyzed Coupling- Isomerization Reaction between Alkynyl Bromides and Propargylic Alcohols.PDF(2049KB)

Abstract

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

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Yang Zonglian, Liao Peiqiu, Li Xingqi, Bi Xihe. Pentynenones Formation through Copper Catalyzed Coupling- Isomerization Reaction between Alkynyl Bromides and Propargylic Alcohols[J]. Chin. J. Org. Chem., 2015, 35(3): 610-617.

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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)

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

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