Visible-Light-Induced Radical [4 + 1] Annulation of Diazosulfonium Triflates with Cyclopropenes: Direct Synthesis of Benzofulvenes

A visible-light-induced radical [4 + 1] annulation of diazosulfonium triflates and cyclopropenes has been established. In this process, diazomethyl radicals generated from diazosulfonium triflates undergo addition to cyclopropenes, followed by ring opening of the resulting cyclopropyl radicals bearing a diazo functionality to form alkenyl radical intermediates, which subsequently participate in intermolecular cyclization. This transformation proceeds under mild reaction conditions and provides an effective approach for the construction of benzofulvene frameworks from easily accessible substrates.

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Publication Details

Journal
Organic Letters
Published
2026-02-13
DOI
https://doi.org/10.1021/acs.orglett.6c00047
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Visible-Light-Induced Radical [4 + 1] Annulation of Diazosulfonium Triflates with Cyclopropenes: Direct Synthesis of Benzofulvenes

Xue‐Cen Xu, Yu-Long Zhao, Yue Gong, Jie Wang
Organic Letters
Radical Photochemical Reactions
article

Visible-Light-Induced Radical [4 + 1] Annulation of Diazosulfonium Triflates with Cyclopropenes: Direct Synthesis of Benzofulvenes

Xue‐Cen Xu, Yu-Long Zhao, Yue Gong, Jie Wang
article en

Abstract

A visible-light-induced radical [4 + 1] annulation of diazosulfonium triflates and cyclopropenes has been established. In this process, diazomethyl radicals generated from diazosulfonium triflates undergo addition to cyclopropenes, followed by ring opening of the resulting cyclopropyl radicals bearing a diazo functionality to form alkenyl radical intermediates, which subsequently participate in intermolecular cyclization. This transformation proceeds under mild reaction conditions and provides an effective approach for the construction of benzofulvene frameworks from easily accessible substrates.

Organic LettersVol. 28(8)
Northeast Normal University (CN), Laboratoire de Synthèse Organique (FR)
Openalex Percentile: Top 54%
Radical Photochemical Reactions
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