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Arylcyanation of Styrenes by Photoactive Electron Donor–Acceptor Complexes/Copper Catalysis

Qilong Wu, Xufeng Li, Jie Ma, Yongjia Shi, Jian Lv, Daoshan Yang

2024Organic Letters25 citationsDOI

Abstract

A novel electron donor-acceptor (EDA) complex/copper catalysis model has been proposed for the construction of 2,3-diarylpropionitriles under visible light conditions. The developed protocol proceeds via intermolecular charge transfer between the photoactive EDA complex of dibutamine (DBA), aryl thianthrenium salts, and trimethylsilyl cyanide (TMSCN), followed by a copper catalytic cycle. UV-vis absorption measurements confirm the participation of EDA complexes as reactive intermediates. This three-component process proceeds smoothly in the presence of pharmaceutically relevant core structures and sensitive functional groups, which offers the possibility of the precise editing of drug molecules with important scaffolds.

Topics & Concepts

ChemistryCatalysisArylPhotochemistryAcceptorCatalytic cycleIntramolecular forceCopperIntermolecular forceCombinatorial chemistryElectron acceptorMoleculeElectron donorCyanideOrganic chemistryCondensed matter physicsAlkylPhysicsRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods
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