Issue 19, 2023

Regio- and chemoselective hydroamination of unactivated alkenes with anthranils via NiH-catalysis

Abstract

A NiH-catalyzed polarity-reversed hydroamination of β,γ-, γ,δ- and δ,ε-unsaturated alkenes with electrophilic anthranils was developed. This reaction proceeds in a highly regio- and chemoselective manner to afford γ, δ and ε-arylamines bearing a carbonyl or alcohol functionality with 100% atom efficiency. Preliminary mechanistic studies indicate that the chemoselectivity is controlled by the base and the alcohol product is derived from the base-catalyzed hydrosilylation of the C[double bond, length as m-dash]O bond.

Graphical abstract: Regio- and chemoselective hydroamination of unactivated alkenes with anthranils via NiH-catalysis

Supplementary files

Article information

Article type
Communication
Submitted
28 Dec 2022
Accepted
31 Jan 2023
First published
06 Feb 2023

Chem. Commun., 2023,59, 2751-2754

Regio- and chemoselective hydroamination of unactivated alkenes with anthranils via NiH-catalysis

Y. Zheng, D. Liang, H. Ma, F. Meng and T. Wang, Chem. Commun., 2023, 59, 2751 DOI: 10.1039/D2CC07052A

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