Copper-catalyzed coupling of tertiary aliphatic amines with terminal alkynes to propargylamines via C-H activation

The Journal of Organic Chemistry
Mingyu NiuYufen Zhao

Abstract

We have developed a convenient and efficient method for coupling of tertiary aliphatic amines with terminal alkynes to propargylamines via C-H activation. The protocol uses CuBr as the catalyst, NBS as the free radical initiator, CH(3)CN as the solvent, and the alkynylation was selectively performed on the methyl of tertiary aliphatic amines at 80 degrees C. This is an economical and practical method for the synthesis of propargylamines.

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Citations

Jun 26, 2009·Organic Letters·Lei Liu, Paul E Floreancig
Feb 14, 2009·Chemical Communications : Chem Comm·Youming ShenCan-Cheng Guo
Aug 12, 2009·Chemical Communications : Chem Comm·Wei Han, Armin R Ofial
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Nov 1, 2011·Chemical Communications : Chem Comm·Ri-Yuan TangJin-Heng Li
Jan 24, 2017·Journal of Computational Chemistry·Haiyan Yuan, Jingping Zhang
Feb 27, 2013·Angewandte Chemie·Deepankar DasDaniel Seidel
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Jan 23, 2014·Chemical Communications : Chem Comm·Mengru LiJingping Zhang
Jun 6, 2013·Organic & Biomolecular Chemistry·Ping HuZhiyong Wang
Sep 24, 2013·Organic & Biomolecular Chemistry·Manman SunWeiliang Bao
Nov 3, 2012·Organic & Biomolecular Chemistry·Tamaki HoshikawaMasayuki Inoue
Nov 23, 2017·Chemical Reviews·Kate LauderDaniele Castagnolo
Mar 21, 2012·Journal of the American Chemical Society·Chuan HeAiwen Lei

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