Catalyst‐Free C<i>sp</i>−C<i>sp</i>³ Cross‐Coupling of Bromodifluoroacetamides with 1‐Iodoalkynes under Visible‐Light Irradiation

Abstract

Abstract 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. magnified image