1,4-Reduction of α,β-Unsaturated Ketones Catalyzed by Tetraarylhydrophosphoranes

Taku Wakabayashi; Jiahua Chen; Bendik Grømer; Shunsuke Chiba

doi:10.1021/acs.orglett.5c02773

1,4-Reduction of α,β-Unsaturated Ketones Catalyzed by Tetraarylhydrophosphoranes

Taku Wakabayashi, Jiahua Chen, Bendik Grømer, Shunsuke Chiba^*

^*Corresponding author for this work

Nanyang Technological University

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

Abstract

We demonstrate that a pentavalent phosphorus compound, tetraarylhydrophosphorane, is capable of catalyzing 1,4-reduction of α,β-unsaturated ketones in the presence of pinacolborane. The structure and properties of tetraarylhydrophosphorane and its participation in the chemoselective 1,4-reduction were elucidated through both experimental and theoretical approaches.

Original language	English
Pages (from-to)	8787-8792
Number of pages	6
Journal	Organic Letters
Volume	27
Issue number	31
DOIs	https://doi.org/10.1021/acs.orglett.5c02773
Publication status	Published - Aug 8 2025
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2025 American Chemical Society

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.5c02773

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AB - We demonstrate that a pentavalent phosphorus compound, tetraarylhydrophosphorane, is capable of catalyzing 1,4-reduction of α,β-unsaturated ketones in the presence of pinacolborane. The structure and properties of tetraarylhydrophosphorane and its participation in the chemoselective 1,4-reduction were elucidated through both experimental and theoretical approaches.

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1,4-Reduction of α,β-Unsaturated Ketones Catalyzed by Tetraarylhydrophosphoranes

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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