A General Platform for Copper-Catalyzed Atom Transfer Radical Addition with Electron-Deficient Olefins

We
disclose a broad platform for copper-catalyzed atom transfer
radical addition (ATRA) of electron-deficient olefins. Catalytic Cu(dtbbpy)2(OTf)2 enables radical addition of electron-deficient
alkyl halides to acrylates, acrylamides, and vinyl sulfones in fair
to excellent yields. The resultant ATRA products can be used in a
variety of telescoped reactions, including substitution with basic
amine nucleophiles to afford α-amino esters. The synthetic utility
of the products is further demonstrated through derivatization to
give substituted cyclopropanes and a γ,δ-unsaturated ester.