Copper‐Catalyzed Hydrodifluoroallylation of Terminal Alkynes to Access (<i>E</i>)‐1,1‐Difluoro‐1,4‐Dienes
Nuo‐Yi Wu, Yangen Huang, Xiu‐Hua Xu, Feng‐Ling Qing
Abstract
Abstract A copper‐catalyzed regio‐ and stereoselective hydrodifluoroallylation of terminal alkynes was disclosed. This reaction employs easily available 3‐bromo‐3,3‐difluoropropene (BDFP) as the difluoroallylating reagent and 1,1,3,3‐tetramethyldisiloxane (TMDSO) as the hydride source, affording a variety of ( E )‐1,1‐difluoro‐1,4‐dienes in moderate to good yields. The synthetic utility of this protocol has been demonstrated through the transformation of resulting ( E )‐1,1‐difluoro‐1,4‐diene to difluoromethylated and trifluoromethylated derivatives. magnified image
Topics & Concepts
ChemistryReagentStereoselectivityCatalysisCopperHydrideDieneTerminal (telecommunication)Organic chemistryMedicinal chemistryCombinatorial chemistryMetalComputer scienceTelecommunicationsNatural rubberFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsCatalytic C–H Functionalization Methods