Copper-catalyzed enantioselective arylalkynylation of alkenes
Guangyue Lei, Hanwen Zhang, Bin Chen, Meichen Xu, Guozhu Zhang
Abstract
A copper-catalyzed enantioselective arylalkynylation of alkenes with diaryliodonium salt and a monosubstituted alkyne is reported. The three-component coupling reactions proceed under mild reaction conditions with a broad substrate scope, leading to synthetically valuable 1,2-diaryl-3-butynes. The key to the success of this chemistry is the employment of the chiral bisoxazoline-phenylaniline (BOPA) ligand. A novel reaction pathway involving the phenyl radical generation under thermal copper catalysis is proposed according to mechanistic studies.
Topics & Concepts
Enantioselective synthesisCatalysisChemistryCopperAlkyneSubstrate (aquarium)Ligand (biochemistry)Combinatorial chemistrySalt (chemistry)Organic chemistryReceptorOceanographyGeologyBiochemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions