Robust Acenaphthoimidazolylidene Palladacycles: Highly Efficient Catalysts for the Amination of N-Heteroaryl Chlorides

Qinyue Deng; Yang Zhang; Haibo Zhu; Tao Tu

doi:10.1002/asia.201700877

Robust Acenaphthoimidazolylidene Palladacycles: Highly Efficient Catalysts for the Amination of N-Heteroaryl Chlorides

Chem Asian J. 2017 Sep 19;12(18):2364-2368. doi: 10.1002/asia.201700877. Epub 2017 Aug 24.

Authors

Qinyue Deng¹, Yang Zhang¹, Haibo Zhu¹, Tao Tu^{1

2}

Affiliations

¹ Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, P.R. China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P.R. China.

PMID: 28719728
DOI: 10.1002/asia.201700877

Abstract

A series of robust N-heterocyclic carbene palladacycles have been successfully developed. These showed high catalytic activity and selectivity toward the challenging amination of N-heteroaryl chlorides. Different primary and secondary amines were fully compatible with this catalytic system. Remarkably, no double amination products could be detected when primary amines were utilized in our catalytic transformation. Furthermore, the protocol has been successfully extended to synthesize rosiglitazone, a clinical drug for diabetes mellitus, highlighting its potential pharmaceutical feasibility.

Keywords: N-heteroaryl chlorides; N-heterocyclic carbenes; amination; carbene ligands; palladium.