Copper-Catalyzed Cross-Coupling of Bicyclobutanes with Triftosylhydrazone Leading to Skipped Dienes
Xiaolong Zhang, Tian Tian, Peiqiu Liao, Zhaohong Liu, Karunanidhi Murali, Xihe Bi
Abstract
Here, we report a protocol for the synthesis of skipped dienes through the cross-coupling of bicyclo[1.1.0]butanes with trifluoromethyl triftosylhydrazones. The reaction is run using Tp Br3 Cu(NCMe) as a catalyst to give access to a library of trifluoromethylated skipped dienes (32 examples, ≤98% yield) with excellent E / Z selectivity under mild and operationally safe conditions. The presented methods proved to be compatible with various functionalized bicyclo[1.1.0]butanes and triftosylhydrazones.
Topics & Concepts
ChemistryYield (engineering)CatalysisSelectivityTrifluoromethylBicyclic moleculeCoupling (piping)Combinatorial chemistryCoupling reactionCopperMedicinal chemistryOrganic chemistryMetallurgyMechanical engineeringMaterials scienceAlkylEngineeringCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry