Ni-Catalyzed Cross-Coupling of Dimethyl Aryl Amines with Arylboronic Esters under Reductive Conditions

Zhi-Chao Cao; Si-Jun Xie; Huayi Fang; Zhang-Jie Shi

doi:10.1021/jacs.8b08779

Ni-Catalyzed Cross-Coupling of Dimethyl Aryl Amines with Arylboronic Esters under Reductive Conditions

J Am Chem Soc. 2018 Oct 24;140(42):13575-13579. doi: 10.1021/jacs.8b08779. Epub 2018 Oct 11.

Authors

Zhi-Chao Cao^{1

2}, Si-Jun Xie¹, Huayi Fang¹, Zhang-Jie Shi^{1

2

3}

Affiliations

¹ Department of Chemistry , Fudan University , Shanghai 200433 , China.
² College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , China.
³ State Key Laboratory of Organometallic Chemistry , Chinese Academy of Science , Shanghai 200032 , China.

PMID: 30289709
DOI: 10.1021/jacs.8b08779

Abstract

Herein, we reported a successful Suzuki-Miyaura coupling of dimethyl aryl amines to forge biaryl skeleton via Ni catalysis in the absence of directing groups and preactivation. This transformation proceeded with high efficiency in the presence of magnesium. Preliminary mechanism studies demonstrated dual roles of magnesium: (i) a reductant that reduced Ni(II) species to active Ni(I) catalyst; (ii) a unique promoter that facilitated the Ni(I)/Ni(III) catalytic cycle.

Publication types

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