Direct C(sp<sup>3</sup>)–H Arylation of Unprotected Benzyl Anilines and Alkylarenes by Organocatalysis under Visible Light
Cheng Huang, Peng Xiao, Zhong-Ming Ye, Chen-Lu Wang, Kang Chen, Sheng Tang, Zhenhong Wei, Hu Cai
Abstract
Reported herein is direct C(sp 3 )–H arylation of unprotected benzyl anilines and alkylarenes via consecutive photoinduced electron transfer by visible light irradiation. Reductive quenching cycles and radical–radical cross-coupling were involved, and electron paramagnetic resonance experiments provide evidence for the formation of radical intermediates formed in situ . The protocol highlights transition metal free, external oxidant free, broad substrate scope, and high efficiency (>60 examples, up to 96%).
Topics & Concepts
ChemistryOrganocatalysisVisible spectrumMedicinal chemistryPhotochromismCatalysisCombinatorial chemistryOrganic chemistryEnantioselective synthesisPhysicsOptoelectronicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques