Copper-Catalyzed Coupling of Alkynes and Amines for the Synthesis of Propargyl Amines in the Presence of PhI(OAc)2

doi:10.6023/cjoc201603003

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (8): 1926-1931.DOI: 10.6023/cjoc201603003 Previous Articles Next Articles

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铜催化、PhI(OAc)₂参与下炔与胺构建炔丙胺类化合物的研究

胡冬燕^a,b, 李孟顺^a,b

a 中国科学院成都有机化学研究所成都 610041;
b 中国科学院大学北京 100049

收稿日期:2016-03-03 修回日期:2016-04-11 发布日期:2016-04-20
通讯作者: 胡冬燕 E-mail:hudy@cib.ac.cn

Copper-Catalyzed Coupling of Alkynes and Amines for the Synthesis of Propargyl Amines in the Presence of PhI(OAc)₂

Hu Dongyan^a,b, Li Mengsun^a,b

a Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041;
b University of the Chinese Academy of Sciences, Beijing 100049

Received:2016-03-03 Revised:2016-04-11 Published:2016-04-20

1. Copper-Catalyzed Coupling of Alkynes and Amines for the Synthesis of Propargyl Amines in the Presence of PhI(OAc)₂.PDF(2272KB)

Abstract

In the presence of iodobenzene diacetate (PhI(OAc)₂), a new CuBr catalyzed coupling reaction of alkynes and amines for the synthesis of propargyl amines was developed. When terminal alkynes, PhI(OAc)₂, and amines were reacted in CH₃CN at 70 ℃ for 3 h under N₂ atmosphere and in the presence of CuBr, the desired propargyl amines were obtained in good yields. Furthermore, no matter aromatic or aliphatic alkynes, were all found to tolerate the reaction conditions. To the best of our knowledge, it is the first time that PhI(OAc)₂ has been used for the synthesis of propargyl amines in one-pot operation from alkynes and amines.

Key words: cuprous bromide, PhI(OAc)₂, propargyl amines

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Hu Dongyan, Li Mengsun. Copper-Catalyzed Coupling of Alkynes and Amines for the Synthesis of Propargyl Amines in the Presence of PhI(OAc)₂[J]. Chin. J. Org. Chem., 2016, 36(8): 1926-1931.

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铜催化、PhI(OAc)₂参与下炔与胺构建炔丙胺类化合物的研究

Copper-Catalyzed Coupling of Alkynes and Amines for the Synthesis of Propargyl Amines in the Presence of PhI(OAc)₂

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铜催化、PhI(OAc)2参与下炔与胺构建炔丙胺类化合物的研究