Reductive Denitration of Nitroarenes

Myuto Kashihara; M. Ramu Yadav; Yoshiaki Nakao

doi:10.1021/acs.orglett.8b00430

Reductive Denitration of Nitroarenes

Myuto Kashihara, M. Ramu Yadav, Yoshiaki Nakao

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

34 Citations (Scopus)

Abstract

The Pd-catalyzed reductive denitration of nitroarenes has been achieved via a direct cleavage of the C-NO₂ bonds. The catalytic conditions reported exhibit a broad substrate scope and good functional-group compatibility. Notably, the use of inexpensive propan-2-ol as a mild reductant suppresses the competitive formation of anilines, which are normally formed by other conventional reductions. Mechanistic studies have revealed that alcohols serve as efficient hydride donors in this reaction, possibly through β-hydride elimination from palladium alkoxides.

Original language	English
Pages (from-to)	1655-1658
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.8b00430
Publication status	Published - Mar 16 2018
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "The Pd-catalyzed reductive denitration of nitroarenes has been achieved via a direct cleavage of the C-NO2 bonds. The catalytic conditions reported exhibit a broad substrate scope and good functional-group compatibility. Notably, the use of inexpensive propan-2-ol as a mild reductant suppresses the competitive formation of anilines, which are normally formed by other conventional reductions. Mechanistic studies have revealed that alcohols serve as efficient hydride donors in this reaction, possibly through β-hydride elimination from palladium alkoxides.",

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

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AU - Yadav, M. Ramu

AU - Nakao, Yoshiaki

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N2 - The Pd-catalyzed reductive denitration of nitroarenes has been achieved via a direct cleavage of the C-NO2 bonds. The catalytic conditions reported exhibit a broad substrate scope and good functional-group compatibility. Notably, the use of inexpensive propan-2-ol as a mild reductant suppresses the competitive formation of anilines, which are normally formed by other conventional reductions. Mechanistic studies have revealed that alcohols serve as efficient hydride donors in this reaction, possibly through β-hydride elimination from palladium alkoxides.

AB - The Pd-catalyzed reductive denitration of nitroarenes has been achieved via a direct cleavage of the C-NO2 bonds. The catalytic conditions reported exhibit a broad substrate scope and good functional-group compatibility. Notably, the use of inexpensive propan-2-ol as a mild reductant suppresses the competitive formation of anilines, which are normally formed by other conventional reductions. Mechanistic studies have revealed that alcohols serve as efficient hydride donors in this reaction, possibly through β-hydride elimination from palladium alkoxides.

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Reductive Denitration of Nitroarenes

Abstract

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