Copper- and Photoredox-Catalyzed Cascade to Trifluoromethylated Divinyl Sulfones
Nejc Petek, Helena Brodnik, Oliver Reiser, Bogdan Štefane
Abstract
A Cu(I)-photoredox-catalyzed trifluoromethylchlorosulfonylation reaction of terminal alkynes under visible light conditions was developed, giving rise to trifluoromethyl-substituted vinylsulfonyl chlorides, which can subsequently be coupled to a second alkyne under photocatalytic conditions. The transformation proceeds with high regio- and stereoselectivity and can be applied to aliphatic and aromatic alkynes with various functional groups. Trifluoromethyl-substituted divinyl sulfones prepared by this protocol can be readily used as synthetically valuable intermediates as demonstrated with various postmodification examples.
Topics & Concepts
TrifluoromethylAlkyneChemistryStereoselectivityPhotoredox catalysisCatalysisCopperPhotocatalysisCascadeCombinatorial chemistryReaction conditionsOrganic chemistryPhotochemistryChromatographyAlkylFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesRadical Photochemical Reactions