Pd/Cu-Catalyzed Vinylation of Terminal Alkynes with (2-Bromoethyl)diphenylsulfonium Triflate
Xiao‐Xia Ming, Shuai Wu, Zeyu Tian, Jia-Wei Song, Cheng‐Pan Zhang
Abstract
The potential of (2-bromoethyl)diphenylsulfonium triflate to be a powerful vinylation reagent was determined by the Sonogashira cross-coupling reactions with terminal alkynes. The vinylation proceeded smoothly at 25 °C under Pd/Cu catalysis to afford a variety of 1- and 2-unsubstituted 1,3-enynes in moderate to excellent yields. This protocol represents the first application of (2-haloethyl)diphenylsulfonium triflate as a CH═CH2 transfer source in organic synthesis.
Topics & Concepts
TrifluoromethanesulfonateChemistrySonogashira couplingCatalysisReagentCombinatorial chemistryTerminal (telecommunication)Medicinal chemistryOrganic chemistryPalladiumComputer scienceTelecommunicationsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesCatalytic Cross-Coupling Reactions