CF<sub>2</sub>Br<sub>2</sub> as a Source for Difluoroolefination of 1,3-Enynes via N-Heterocyclic Carbene Catalysis
Lei Chen, Jingyi Wang, Lin Chen, Yi‐Wei Zhu, Ding Du
Abstract
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.
Topics & Concepts
ChemistryCarbeneCatalysisAlleneCombinatorial chemistryCascadeSubstrate (aquarium)Surface modificationOrganic chemistryOceanographyChromatographyGeologyPhysical chemistryFluorine in Organic ChemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCyclopropane Reaction Mechanisms