Visible-Light-Induced [2 + 2] Cyclization of Alkynes with Bromodifluoroacetylsilanes: Facile Access to <i>gem</i>-Difluorocyclobutenones

Herein, we report a simple and efficient method for the synthesis of <i>gem</i>-difluorocyclobutenones from alkynes and bromodifluoroacetylsilanes, proceeding via a formal cyclization with <i>in situ</i> generated difluoroketene under visible-light-induced conditions. The reaction conditions are mild and exhibit a broad substrate scope, including both aromatic and aliphatic alkynes. Additionally, the reaction demonstrates good functional group tolerance, facile scalability, and the potential for diverse downstream transformations. Mechanistic studies suggest that bromodifluoroacetylsilanes act as photochemical precursors to difluoroketene.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2025-04-29
DOI
https://doi.org/10.1021/jacs.5c03504
Citations
19
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
15.02

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article

Visible-Light-Induced [2 + 2] Cyclization of Alkynes with Bromodifluoroacetylsilanes: Facile Access to gem-Difluorocyclobutenones

Gang Zhou, Xiao Shen, Xiaoqian He, Ying Liu et al.
19 citations
Journal of the American Chemical Society
Fluorine in Organic Chemistry
15.02
article

Visible-Light-Induced [2 + 2] Cyclization of Alkynes with Bromodifluoroacetylsilanes: Facile Access to gem-Difluorocyclobutenones

Gang Zhou, Xiao Shen, Xiaoqian He, Ying Liu, Shanshan Liu, Yongpeng Li
article en
19 citations

Abstract

Herein, we report a simple and efficient method for the synthesis of <i>gem</i>-difluorocyclobutenones from alkynes and bromodifluoroacetylsilanes, proceeding via a formal cyclization with <i>in situ</i> generated difluoroketene under visible-light-induced conditions. The reaction conditions are mild and exhibit a broad substrate scope, including both aromatic and aliphatic alkynes. Additionally, the reaction demonstrates good functional group tolerance, facile scalability, and the potential for diverse downstream transformations. Mechanistic studies suggest that bromodifluoroacetylsilanes act as photochemical precursors to difluoroketene.

Journal of the American Chemical SocietyVol. 147(19)
Wuhan University (CN)
National Natural Science Foundation of China, China Postdoctoral Science Foundation, National Key Research and Development Program of China
Openalex Percentile: Top 1%
Fluorine in Organic Chemistry
15.02
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