Cyclic Amine Synthesis via Catalytic Radical-Polar Crossover Cycloadditions

The rapid assembly of valuable cyclic amine architectures in a single step from simple precursors has been recognized as an ideal platform in term of efficiency and sustainability. Although a vast number of studies regarding cyclic amine synthesis has been reported, new synthetic disconnection approaches are still high in demand. Herein, we report a catalytic radical-polar crossover cycloaddition to cyclic amine synthesis triggered from primary sulfonamide under photoredox condition. This newly developed disconnection, comparable to established synthetic approaches, will allow to construct beta, beta-disubstituted cyclic amine and beta-monosubstituted cyclic amine derivatives efficiently. This study highlights the unique utility of primary sulfonamide as a bifunctional reagent, which acts as a radical precursor and a nucleophile. The open-shell methodology demonstrates broad tolerance to various functional groups, drug derivatives and natural products in an economically and sustainable fashion. Cyclic amine synthesis has been achieved by a catalytic radical-polar crossover cycloaddition (RPCC) triggered from primary sulfonamide under photoredox condition. The newly developed disconnection allows to construct beta, beta-disubstituted and beta-monosubstituted cyclic amines. This study highlights the unique utility of primary sulfonamides as bifunctional reagents, which act as radical precursors and nucleophiles. image