Light-Promoted C-N Coupling of Aryl Halides with Nitroarenes



Li, Gang, Yang, Liu, Liu, Jian-Jun, Zhang, Wei, Cao, Rui, Wang, Chao, Zhang, Zunting, Xiao, Jianliang ORCID: 0000-0003-2010-247X and Xue, Dong
(2021) Light-Promoted C-N Coupling of Aryl Halides with Nitroarenes. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 60 (10). pp. 5230-5234.

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Abstract

A photochemical C-N coupling of aryl halides with nitroarenes is demonstrated for the first time. Catalyzed by a Ni<sup>II</sup> complex in the absence of any external photosensitizer, readily available nitroarenes undergo coupling with a variety of aryl halides, providing a step-economic extension to the widely used Buchwald-Hartwig C-N coupling reaction. The method tolerates coupling partners with steric-congestion and functional groups sensitive to bases and nucleophiles. Mechanistic studies suggest that the reaction proceeds via the addition of an aryl radical, generated from a Ni<sup>I</sup> /Ni<sup>III</sup> cycle, to a nitrosoarene intermediate.

Item Type: Article
Uncontrolled Keywords: amination, aryl halides, aryl radicals, nickel catalysis, nitroarenes
Depositing User: Symplectic Admin
Date Deposited: 30 Nov 2020 09:23
Last Modified: 18 Jan 2023 23:20
DOI: 10.1002/anie.202012877
Related URLs:
URI: https://livrepository.liverpool.ac.uk/id/eprint/3108510