Photocatalytic Oxidative Generation and Synthetic Application of Phosphine–Boryl Radicals

Phosphine-boryl radicals remain less well-studied because their parent phosphine-boranes are highly stable under oxidative conditions. Herein, we report a strategy for generating phosphine-boryl radicals facilitated by radical precursors through an appropriate molecular design. Incorporating a proximal oxidant into a phosphine-borane facilitates the formation of the corresponding boron-centered radical through proton-coupled intramolecular electron transfer. The resulting phosphine-boryl radical can be used to generate an alkyl radical via halogen atom transfer.

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Publication Details

Journal
Organic Letters
Published
2026-04-24
DOI
https://doi.org/10.1021/acs.orglett.6c01460
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Photocatalytic Oxidative Generation and Synthetic Application of Phosphine–Boryl Radicals

Tetsuhiro Nemoto, Takahito Kuribara, Yu Matsuda
Organic Letters
Radical Photochemical Reactions
article

Photocatalytic Oxidative Generation and Synthetic Application of Phosphine–Boryl Radicals

Tetsuhiro Nemoto, Takahito Kuribara, Yu Matsuda
article en

Abstract

Phosphine-boryl radicals remain less well-studied because their parent phosphine-boranes are highly stable under oxidative conditions. Herein, we report a strategy for generating phosphine-boryl radicals facilitated by radical precursors through an appropriate molecular design. Incorporating a proximal oxidant into a phosphine-borane facilitates the formation of the corresponding boron-centered radical through proton-coupled intramolecular electron transfer. The resulting phosphine-boryl radical can be used to generate an alkyl radical via halogen atom transfer.

Organic LettersVol. 28(18)
Chiba University (JP)
Japan Society for the Promotion of Science
Openalex Percentile: Top 20%
Radical Photochemical Reactions
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