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Photoinduced Triphenylphosphine and Iodide Salt Promoted Reductive Decarboxylative Coupling

Jiaxin Wang, Ming‐Chen Fu, Lu‐Yu Yan, Xi Lu, Yao Fu

2024Advanced Science31 citationsDOIOpen Access PDF

Abstract

The transient electron donor-acceptor (EDA) complex has been an emerging area in the photoinduced organic synthesis field, generating radicals without exogenous transition-metal or organic dye-based photoredox catalysts. The catalytic platform to form suitable photoactive EDA complexes for photochemical reduction reactions remains underdeveloped. Herein, a general photoinduced reductive alkylation via the EDA complex strategy is described. A simple yet multifunctional system, triphenylphosphine and iodide salt, promotes the photoinduced decarboxylative hydroalkylation, and reductive defluorinative decarboxylative alkylation of trifluoromethyl alkenes, to access trifluoromethyl alkanes and gem-difluoroalkenes. Moreover, decarboxylative hydroalkylation can be applied to more kinds of electron-deficient alkenes as a general Giese addition reaction.

Topics & Concepts

TrifluoromethylAlkylationTriphenylphosphineReductive eliminationIodideChemistryPhotochemistryCatalysisCombinatorial chemistryHalogenationOrganic chemistryAlkylFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods