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Light‐Promoted C–N Coupling of Aryl Halides with Nitroarenes
Author(s) -
Li Gang,
Yang Liu,
Liu JianJun,
Zhang Wei,
Cao Rui,
Wang Chao,
Zhang Zunting,
Xiao Jianliang,
Xue Dong
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202012877
Subject(s) - halide , aryl , chemistry , steric effects , nucleophile , photochemistry , coupling (piping) , coupling reaction , combinatorial chemistry , catalysis , medicinal chemistry , organic chemistry , materials science , alkyl , metallurgy
A photochemical C–N coupling of aryl halides with nitroarenes is demonstrated for the first time. Catalyzed by a Ni II 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 I /Ni III cycle, to a nitrosoarene intermediate.