Three‐Component Aminoarylation of Electron‐Rich Alkenes by Merging Photoredox with Nickel Catalysis

Abstract

AbstractA three‐component 1,2‐aminoarylation of vinyl ethers, enamides, ene‐carbamates and vinyl thioethers by synergistic photoredox and nickel catalysis is reported. 2,2,2‐Trifluoroethoxy carbonyl protected α‐amino‐oxy acids are used as amidyl radical precursors. anti‐Markovnikov addition of the amidyl radical to the alkene and Ni‐mediated radical/transition metal cross over lead to the corresponding 1,2‐aminoarylation product. The radical cascade, which can be conducted under practical and mild conditions, features high functional group tolerance and broad substrate scope. Stereoselective 1,2‐aminoarylation is achieved using a L‐(+)‐lactic acid derived vinyl ether as the substrate, offering a novel route for the preparation of protected enantiopure α‐arylated β‐amino alcohols. In addition, 1,2‐aminoacylation of vinyl ethers is achieved by using an acyl succinimide as the electrophile for the Ni‐mediated radical coupling.