Organophotoredox catalysis in C–C cross-coupling reactions by a phosphonium ylide

Abstract Organophotoredox-catalyzed cross-coupling reactions between aryl halides and N-methylpyrroles are demonstrated. The excited state of a phosphonium ylide reduces the aryl halides to generate the corresponding aryl radicals that add to N-methylpyrrole. A series of 2-arylated pyrroles were obtained in moderate to good yields in the presence of a phosphonium ylide catalyst under visible-light irradiation. This protocol can be applied not only to the reactions of 1,3-dimethylindole but also to the reactions of 1,3,5-trimethoxybenzene.

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Publication Details

Journal
Chemistry Letters
Published
2026-05-27
DOI
https://doi.org/10.1093/chemle/upag097
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Organophotoredox catalysis in C–C cross-coupling reactions by a phosphonium ylide

Yasunori Toda, Rintaro Komatsu, Sota Fuwa
Chemistry Letters
Radical Photochemical Reactions
article

Organophotoredox catalysis in C–C cross-coupling reactions by a phosphonium ylide

Yasunori Toda, Rintaro Komatsu, Sota Fuwa
article en

Abstract

Abstract Organophotoredox-catalyzed cross-coupling reactions between aryl halides and N-methylpyrroles are demonstrated. The excited state of a phosphonium ylide reduces the aryl halides to generate the corresponding aryl radicals that add to N-methylpyrrole. A series of 2-arylated pyrroles were obtained in moderate to good yields in the presence of a phosphonium ylide catalyst under visible-light irradiation. This protocol can be applied not only to the reactions of 1,3-dimethylindole but also to the reactions of 1,3,5-trimethoxybenzene.

Chemistry Letters
Shinshu University (JP)
Clean water and sanitation
Openalex Percentile: Top 10%
Radical Photochemical Reactions
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