Reductive Denitration of Nitroarenes

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...

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Bibliographic Details
Published in:Organic letters 2018-03, Vol.20 (6), p.1655-1658
Main Authors: Kashihara, Myuto, Yadav, M. Ramu, Nakao, Yoshiaki
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00430