Doyle–Kirmse reaction using 3,3-difluoroallyl sulfide and <i>N</i>-sulfonyl-1,2,3-triazole: an efficient access to <i>gem</i>-difluoroallylated multifunctional quaternary carbon
Jiazhuang Wang, Jingwen Yu, Junyu Chen, Yubo Jiang, Tiebo Xiao
Abstract
A Doyle-Kirmse reaction of N-sulfonyl-1,2,3-triazole with 3,3-difluoroallyl sulfide through a Rh(ii)-catalyzed [2,3]-sigmatropic rearrangement has been developed, which provides an efficient access to multifunctional quaternary centers containing aryl, imino, thio, and brominated gem-difluoroallyl groups. The reaction features broad substrate scope with moderate to excellent yields. The applicability of the method is confirmed by gram-scale synthesis and further transformations.
Topics & Concepts
ChemistrySulfonylSubstrate (aquarium)Combinatorial chemistryArylThio-SulfideQuaternary carbonMedicinal chemistryTriazoleInsertion reactionCatalysisOrganic chemistryEnantioselective synthesisAlkylOceanographyGeologyCyclopropane Reaction MechanismsFluorine in Organic ChemistrySulfur-Based Synthesis Techniques