Photoinduced Intermolecular Radical Hydroalkylation of Olefins via Ligated Boryl Radicals-Mediated Halogen Atom Transfer
Ting Wan, Łukasz W. Ciszewski, Davide Ravelli, Luca Capaldo
Abstract
Light-mediated Halogen-Atom Transfer (XAT) has become a significant methodology in contemporary synthesis. Unlike α-aminoalkyl and silyl radicals, ligated boryl radicals (LBRs) have not been extensively explored as halogen atom abstractors. In this study, we introduce NHC-ligated boranes as optimal radical chain carriers for the intermolecular reductive radical hydroalkylation and hydroarylation of electron-deficient olefins by using direct UV-A light irradiation. DFT analysis allowed us to rationalize the critical role of the NHC ligand in facilitating efficient chain propagation.
Topics & Concepts
ChemistryRadicalIntermolecular forceHalogenPhotochemistryPhotoinduced electron transferTriethylboraneAtom (system on chip)Atom-transfer radical-polymerizationElectron transferCombinatorial chemistryCatalysisOrganic chemistryMoleculeAlkylComputer scienceCopolymerPolymerEmbedded systemRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry