Generation of Alkyl Radicals from Thiols via Zinc Thiolates: Application for the Synthesis of <i>gem</i>‐Difluorostyrenes
Vyacheslav I. Supranovich, Vitalij V. Levin, Vladimir A. Kokorekin, Alexander D. Dilman
Abstract
Abstract Reaction of thiols with α‐(trifluoromethyl)styrenes under photocatalytic conditions leading to desulfurative allylic fluorine substitution is described. The reaction is performed by treatment of thiols with benzyl zinc chloride to generate zinc thiolates followed by visible light induced desulfurization by means of triphenylphosphine. Radicals formed after the C−S bond cleavage react with the double bond affording gem ‐difluorostyrenes. magnified image
Topics & Concepts
ChemistryAllylic rearrangementZincTrifluoromethylRadicalPhotocatalysisTriphenylphosphineAlkylPhotochemistryFluorineOrganic chemistryMedicinal chemistryCatalysisFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesRadical Photochemical Reactions