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, M. Rueping
Chemical Science, Volume 10, Issue 16, 2019, Pages 4430-4435, (2019)

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

Keywords

Reductive cross, Functional theory

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.

Code

DOI: 10.1039/C9SC00783K

Sources

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