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Journal Of Organic Chemistry

Publication date: 2019-08-16
Volume: 84 Pages: 10501 - 10508
Publisher: American Chemical Society

Author:

Li, Huiqiong
Feng, Huangdi ; Zhang, Jingxian ; Van Der Eycken, Erik V ; Huang, Liliang

Keywords:

Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, ALDEHYDE-ALKYNE-AMINE, AEROBIC OXIDATION, TERTIARY-AMINES, TERMINAL ALKYNES, EFFICIENT, IMINES, METAL, HYDROAMINATION, ACTIVATION, HETEROCYCLES, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

Abstract:

A novel and selective cascade reaction of primary amines and alkynes for the synthesis of the corresponding secondary propargylamines is described. This protocol proceeds with a CuBr2/TBHP system through a process of oxidative deamination of primary amines to imine and alkynylation, featuring a wide scope of substrates with good functional-group tolerance and operational simplicity. Additionally, the use of two different primary amines could also work smoothly using this protocol.