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

Yan-Long Zheng; Di-Yu Liang; Hong-Bin Ma; Fan-Cheng Meng; Tie Wang

doi:10.1039/d2cc07052a

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

Chem Commun (Camb). 2023 Mar 2;59(19):2751-2754. doi: 10.1039/d2cc07052a.

Authors

Yan-Long Zheng¹, Di-Yu Liang¹, Hong-Bin Ma¹, Fan-Cheng Meng¹, Tie Wang¹

Affiliation

¹ Tianjin Key Laboratory of Drug Targeting and Bioimaging, Life and Health Intelligent Research Institute, Tianjin University of Technology, Tianjin, 300384, P. R. China. ylzheng@email.tjut.edu.cn.

PMID: 36779354
DOI: 10.1039/d2cc07052a

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O bond.