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.
Authors
- Gang Zhou (ORCID: https://orcid.org/0000-0003-4988-0814)
- Xiao Shen (ORCID: https://orcid.org/0000-0002-8675-1213)
- Xiaoqian He
- Ying Liu (ORCID: https://orcid.org/0000-0001-9862-5786)
- Shanshan Liu (ORCID: https://orcid.org/0000-0002-0806-7918)
- Yongpeng Li (ORCID: https://orcid.org/0000-0002-1104-1129)
Institutions
- Wuhan University (CN)
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
Funders
- National Natural Science Foundation of China
- China Postdoctoral Science Foundation
- National Key Research and Development Program of China