Substrate Redox Non-innocence Inducing Stepwise Oxidative Addition Reaction: Nitrosoarene C–N Bond Cleavage on Low-Coordinate Cobalt(0) Species

Substrate Redox Non-innocence Inducing Stepwise Oxidative Addition Reaction: Nitrosoarene C–N Bond Cleavage on Low-Coordinate Cobalt(0) Species

The reactions of nitroso­arenes with transition-metal species are fundamentally important for their relevance to metal-catalyzed transformations of organo-nitrogen compounds in organic synthesis and also the metabolization of nitroarenes and anilines in biology. In addition to the well-known reactiv...

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Veröffentlicht in:Journal of the American Chemical Society 2019-05, Vol.141 (19), p.7731-7735
Hauptverfasser: Wang, Dongyang, Leng, Xuebing, Ye, Shengfa, Deng, Liang
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container_end_page 7735
container_issue 19
container_start_page 7731
container_title Journal of the American Chemical Society
container_volume 141
creator Wang, Dongyang
Leng, Xuebing
Ye, Shengfa
Deng, Liang
description The reactions of nitroso­arenes with transition-metal species are fundamentally important for their relevance to metal-catalyzed transformations of organo-nitrogen compounds in organic synthesis and also the metabolization of nitroarenes and anilines in biology. In addition to the well-known reactivity of metal-mediated N–O bond activation and cleavage of nitroso­arenes, we present herein the first observation of a nitroso­arene C–N bond oxidative addition reaction upon the interaction of a three-coordinate cobalt(0) species [(IPr)­Co­(vtms)2] with 2,4,6-tri­(tert-butyl)-1-nitroso-benzene (Ar*NO). The reaction produces a cobalt nitrosyl aryl complex, [(IPr)­Co­(Ar*)­(NO)] (1), with a bis­(nitroso­arene)cobalt complex, [(IPr)­Co­(η2-ONAr)­(κ1-O-ONAr)] (2), as an intermediate. Spectroscopic characterizations, DFT calculations, and kinetic studies revealed that the redox non-innocence of nitroso­arene induces a stepwise pathway for the C–N bond oxidative addition reaction.
doi_str_mv 10.1021/jacs.9b03726
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title Substrate Redox Non-innocence Inducing Stepwise Oxidative Addition Reaction: Nitrosoarene C–N Bond Cleavage on Low-Coordinate Cobalt(0) Species
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