Fluoroamide-driven intermolecular hydrogen-atom-transfer-enabled intermolecular 1,2-alkylarylation of alkenes

Abstract

A new fluoroamide-driven intermolecular hydrogen atom transfer (HAT) strategy for the copper-catalyzed intermolecular 1,2-alkylarylation of alkenes with carbazates and various arene nucleophiles, such as indoles, pyrroles and 1,3,5-trimethoxybenzene, is described. By using N-(tert-butyl)-N-fluoro-3,5-bis(trifluoromethyl)benzenesulfonamide (NFBS) as the intermolecular HAT reagent, this reaction enables the generation of carbazate nitrogen-centered radicals through intermolecular HAT followed by decomposition to form alkyl radicals, radical addition across the alkene, single electron oxidation and nucleophilic coupling cascades to achieve the alkene 1,2-alkylarylation.