Selective Synthesis of Quaternary Carbon Propargylamines from Amines, Alkynes, and Alkynes under Neat Condition

doi:10.6023/cjoc201805033

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (10): 2639-2647.DOI: 10.6023/cjoc201805033 Previous Articles Next Articles

Articles

无溶剂下胺、炔、炔反应选择性构筑季碳炔丙基胺

王峥^a, 杨柳^a, 刘慧兰^a, 谭英芝^a, 包文虎^a, 汪明^b, 唐子龙^b, 何卫民^a

a 湖南省银杏工程技术研究中心湖南科技学院永州 425100;
b 理论有机化学与功能分子教育部重点实验室湖南科技大学湘潭 411201

收稿日期:2018-05-16 修回日期:2018-06-08 发布日期:2018-06-15
通讯作者: 何卫民,E-mail:weiminhe2016@yeah.net E-mail:weiminhe2016@yeah.net
基金资助:
国家自然科学基金（Nos.21877034）资助项目.

Selective Synthesis of Quaternary Carbon Propargylamines from Amines, Alkynes, and Alkynes under Neat Condition

Wang Zheng^a, Yang Liu^a, Liu Huilan^a, Bao Wenhu^a, Tan Yingzhi^a, Wang Ming^b, Tang Zilong^b, He Weimin^a

a Hunan Provincial Engineering Research Center for Ginkgo biloba, Hunan University of Science and Engineering, Yongzhou 425100;
b Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201

Received:2018-05-16 Revised:2018-06-08 Published:2018-06-15
Contact: 10.6023/cjoc201805033 E-mail:weiminhe2016@yeah.net
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21877034).

1. Selective Synthesis of Quaternary Carbon Propargylamines from Amines, Alkynes, and Alkynes under Neat Condition.PDF(16780KB)

Abstract

An efficient and facile method has been developed for the synthesis of quaternary carbon propargylamines via a one-pot tandem reaction of amines, alkynes, and alkynes under neat condition. Both aliphatic and aromatic terminal alkynes are well compatible with the established reaction, with respect to aliphatic alkynes, AgOTf was used as catalyst for the Markovnikov amine-alkyne-alkyne coupling process. When aromatic alkynes were used as substrates, the reaction was promoted by CuBr₂/Zn (OTf)₂ co-catalytic system. This tandem reaction exhibits excellent atom efficiency and provides an attractive approach to a diverse range of quaternary carbon propargylamines.

Key words: propargylamines, quaternary carbon, alkynes, neat condition, green organic synthesis

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Wang Zheng, Yang Liu, Liu Huilan, Bao Wenhu, Tan Yingzhi, Wang Ming, Tang Zilong, He Weimin. Selective Synthesis of Quaternary Carbon Propargylamines from Amines, Alkynes, and Alkynes under Neat Condition[J]. Chin. J. Org. Chem., 2018, 38(10): 2639-2647.

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无溶剂下胺、炔、炔反应选择性构筑季碳炔丙基胺

Selective Synthesis of Quaternary Carbon Propargylamines from Amines, Alkynes, and Alkynes under Neat Condition

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