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Catalyst-Free Csp−Csp^3 Cross-Coupling of Bromodifluoroacetamides with 1-Iodoalkynes under Visible-Light Irradiation

Yamamoto, Yoshihiko Kuroyanagi, Eisuke Suzuki, Harufumi Yasui, Takeshi 名古屋大学

2021.11.09

概要

We describe herein that the cross-coupling of bromodifluoroacetamides with (iodoethynyl)arenes proceeds without recourse to any photocatalyst when exposed to visible light at room temperature to afford alkynyldifluoroacetamides in 62–83% yields (27 examples). Several control experiments suggest that the reaction involves the homolysis of bromodifluoroacetamides and the coupling of the resultant difluoromethyl radical species with the 1-iodoalkynes via a radical chain process. Divergent transformations of the coupling products led to various organofluorine compounds, demonstrating the synthetic utility of the developed photo-coupling method.

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