Issue 16, 2019

Nickel-catalyzed C–N bond activation: activated primary amines as alkylating reagents in reductive cross-coupling

Abstract

Nickel-catalyzed reductive cross coupling of activated primary amines with aryl halides under mild reaction conditions has been achieved for the first time. Due to the avoidance of stoichiometric organometallic reagents and external bases, the scope regarding both coupling partners is broad. Thus, a wide range of substrates, natural products and drugs with diverse functional groups are tolerated. Moreover, experimental mechanistic investigations and density functional theory (DFT) calculations in combination with wavefunction analysis have been performed to understand the catalytic cycle in more detail.

Graphical abstract: Nickel-catalyzed C–N bond activation: activated primary amines as alkylating reagents in reductive cross-coupling

Supplementary files

Article information

Article type
Edge Article
Submitted
14 Feb 2019
Accepted
12 Mar 2019
First published
20 Mar 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 4430-4435

Nickel-catalyzed C–N bond activation: activated primary amines as alkylating reagents in reductive cross-coupling

H. Yue, C. Zhu, L. Shen, Q. Geng, K. J. Hock, T. Yuan, L. Cavallo and M. Rueping, Chem. Sci., 2019, 10, 4430 DOI: 10.1039/C9SC00783K

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