CF2Br2 as a Source for Difluoroolefination of 1,3-Enynes via N-Heterocyclic Carbene Catalysis

Commercially available CF2Br2 has been used as a convenient source for the rapid and reliable incorporation of the gem-difluorovinyl motif into an allene framework via an N-heterocyclic carbene catalyzed difluoroolefination of 1,3-enynes. The reaction proceeds through a cascade three-component radical relay/elimination process. This protocol is distinguished by its mild conditions, readily accessible starting materials, wide substrate scope, and ease of late-stage functionalization, thus unlocking an untraditional strategy to construct a new class of functionalized gem-difluorovinyl allenes.