Palladium-Catalyzed Difluorocarbene Transfer Enabled Divergent Synthesis of γ‑Butenolides and Ynones from Iodobenzene and Terminal Alkynes

Herein, we report a ligand-controlled palladium-catalyzed method that enables the synthesis of ynones and γ-butenolides with excellent regioselectivity from the same set of readily available aryl iodides, aryl acetylenes, and BrCF2CO2K. In this reaction, the [PdII]CF2 does demonstrate electrophilic...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2024-01, Vol.146 (2), p.1722-1731
Main Authors: Sheng, Heyun, Chen, Zhiwei, Song, Qiuling
Format: Article
Language:English
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Summary:Herein, we report a ligand-controlled palladium-catalyzed method that enables the synthesis of ynones and γ-butenolides with excellent regioselectivity from the same set of readily available aryl iodides, aryl acetylenes, and BrCF2CO2K. In this reaction, the [PdII]CF2 does demonstrate electrophilicity and can generate CO readily when reacting with H2O. It is environmentally friendly and safe compared to traditional methods, and the current protocol enables us to afford ynones and γ-butenolides in high yields with excellent functionality tolerance. Moreover, esters can also be obtained with corresponding phenols and alcohols utilizing this strategy. The success of late-stage functionalization of bioactive compounds further illustrates the synthetic utility of this protocol in material development and drug discovery.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.3c13044