Buchwald–Hartwig Amination of Nitroarenes

Fumiyoshi Inoue; Myuto Kashihara; M. Ramu Yadav; Yoshiaki Nakao

doi:10.1002/anie.201706982

Buchwald–Hartwig Amination of Nitroarenes

Fumiyoshi Inoue, Myuto Kashihara, M. Ramu Yadav, Yoshiaki Nakao

Research output: Contribution to journal › Article › peer-review

73 Citations (Scopus)

Abstract

The Buchwald–Hartwig amination of nitroarenes was achieved for the first time by using palladium catalysts bearing dialkyl(biaryl)phosphine ligands. These cross-coupling reactions of nitroarenes with diarylamines, arylamines, and alkylamines afforded the corresponding substituted arylamines. A catalytic cycle involving the oxidative addition of the Ar−NO₂ bond to palladium(0) followed by nitrite/amine exchange is proposed based on a stoichiometric reaction.

Original language	English
Pages (from-to)	13307-13309
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	43
DOIs	https://doi.org/10.1002/anie.201706982
Publication status	Published - Oct 16 2017
Externally published	Yes

Keywords

amination
cross-coupling
C−N activation
nitroarenes
palladium

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201706982

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abstract = "The Buchwald–Hartwig amination of nitroarenes was achieved for the first time by using palladium catalysts bearing dialkyl(biaryl)phosphine ligands. These cross-coupling reactions of nitroarenes with diarylamines, arylamines, and alkylamines afforded the corresponding substituted arylamines. A catalytic cycle involving the oxidative addition of the Ar−NO2 bond to palladium(0) followed by nitrite/amine exchange is proposed based on a stoichiometric reaction.",

keywords = "amination, cross-coupling, C−N activation, nitroarenes, palladium",

author = "Fumiyoshi Inoue and Myuto Kashihara and Yadav, {M. Ramu} and Yoshiaki Nakao",

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doi = "10.1002/anie.201706982",

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AU - Inoue, Fumiyoshi

AU - Kashihara, Myuto

AU - Yadav, M. Ramu

AU - Nakao, Yoshiaki

N1 - Funding Information: This work was supported by JST CREST Grant JPMJCR14L3 (“Establishment of Molecular Technology towards the Creation of New Functions”), JSPS KAKENHI Grant JP15H05799 (“Precisely Designed Catalysts with Customized Scaffolding”), and TOSOH Corporation. Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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Y1 - 2017/10/16

N2 - The Buchwald–Hartwig amination of nitroarenes was achieved for the first time by using palladium catalysts bearing dialkyl(biaryl)phosphine ligands. These cross-coupling reactions of nitroarenes with diarylamines, arylamines, and alkylamines afforded the corresponding substituted arylamines. A catalytic cycle involving the oxidative addition of the Ar−NO2 bond to palladium(0) followed by nitrite/amine exchange is proposed based on a stoichiometric reaction.

AB - The Buchwald–Hartwig amination of nitroarenes was achieved for the first time by using palladium catalysts bearing dialkyl(biaryl)phosphine ligands. These cross-coupling reactions of nitroarenes with diarylamines, arylamines, and alkylamines afforded the corresponding substituted arylamines. A catalytic cycle involving the oxidative addition of the Ar−NO2 bond to palladium(0) followed by nitrite/amine exchange is proposed based on a stoichiometric reaction.

KW - amination

KW - cross-coupling

KW - C−N activation

KW - nitroarenes

KW - palladium

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Buchwald–Hartwig Amination of Nitroarenes

Abstract

Keywords

ASJC Scopus subject areas

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