Iron-Catalyzed Reductive Vinylation of Tertiary Alkyl Oxalates with Activated Vinyl Halides
Yang Ye, Haifeng Chen, Ken Yao, Hegui Gong
Abstract
We present herein a rare and efficient method for the creation of vinylated all carbon quaternary centers via Fe-catalyzed cross-electrophile coupling of vinyl halides with tertiary alkyl methyl oxalates. The reaction displays excellent functional group tolerance and broad substrate scope, which allows cascade radical cyclization and vinylation to afford complex bicyclic and spiral structural motifs. The reaction proceeds via tertiary alkyl radicals, and the putative vinyl-Br/Fe complexation appears to be crucial for activating the alkene and enabling a possibly concerted radical addition/C-Fe forming process.
Topics & Concepts
ChemistryAlkylAlkeneCatalysisHalideElectrophileMedicinal chemistryRadicalOrganic chemistryCombinatorial chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions