Visible-Light Photocatalytic and Phosphine-Mediated In Situ Wittig Reaction of Bicyclo[1.1.0]butanes with Aryl Aldehydes

Organic Letters 2026

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Authors: He‐Xiang Dang, Jing-Jie Ming, Yi-Hao Jin, Wen-Hao Wang, Dong-Sen Duan, Qi Wang, Liang Ping, Wen Bao, Ye Zhang, Dao‐Yong Zhu, S K Wang
DOI: 10.1021/acs.orglett.6c01971
Cited by: 1
References: 54

Abstract

This study reports a new strategy for the in situ Wittig olefination of bicyclo[1.1.0]butanes (BCBs) with aryl aldehydes, enabled by the synergistic combination of blue light photocatalysis and phosphine mediation. This reaction proceeds under mild and efficient conditions, enabling the direct construction of arylidenecyclobutane scaffolds. Mechanistic investigations revealed that the photoinduced phosphine radical effectively activates the highly strained BCB skeleton, triggering ring opening and the in situ formation of a key ylide intermediate, which subsequently undergoes olefination. This method demonstrates good functional group compatibility, offering a new approach to the precise functionalization of strained carbocycles and the modular synthesis of complex alkene architectures.

Fields of Study & Subjects

Radical Photochemical Reactions Phosphorus compounds and reactions Asymmetric Hydrogenation and Catalysis

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
24
Pages
7760–7765
Publication date
8 June 2026
Language
EN