Directed nickel-catalyzed regio- and diastereoselective arylamination of unactivated alkenes

Leipeng Xie; Shenghao Wang; Lanlan Zhang; Lei Zhao; Chun Luo; Linping Mu; Xiuguang Wang; Chao Wang

doi:10.1038/s41467-021-26527-x

Directed nickel-catalyzed regio- and diastereoselective arylamination of unactivated alkenes

Nat Commun. 2021 Nov 1;12(1):6280. doi: 10.1038/s41467-021-26527-x.

Authors

Leipeng Xie^#¹, Shenghao Wang^#¹, Lanlan Zhang^#¹, Lei Zhao¹, Chun Luo¹, Linping Mu¹, Xiuguang Wang¹, Chao Wang²

Affiliations

¹ Tianjin Key Laboratory of Structure and Performance for Functional Molecules; College of Chemistry, Tianjin Normal University, Tianjin, 300387, People's Republic of China.
² Tianjin Key Laboratory of Structure and Performance for Functional Molecules; College of Chemistry, Tianjin Normal University, Tianjin, 300387, People's Republic of China. chwang@tjnu.edu.cn.

^# Contributed equally.

Abstract

Few methods have been reported for intermolecular arylamination of alkenes, which could provide direct access to important arylethylamine scaffolds. Herein, we report an intermolecular syn-1,2-arylamination of unactivated alkenes with arylboronic acids and O-benzoylhydroxylamine electrophiles with Ni(II) catalyst. The cleavable bidentate picolinamide directing group facilitates formation of stabilized 4-, 5- or 6-membered nickelacycles and enables the difunctionalization of diverse alkenyl amines with high levels of regio-, chemo- and diastereocontrol. This general and practical protocol is compatible with broad substrate scope and high functional group tolerance. The utility of this method is further demonstrated by the site-selective modification of pharmaceutical agents.

Publication types

Research Support, Non-U.S. Gov't