Purple‐Light Promoted Thiol‐ene Reaction of Alkenes
Polyssena Renzi, Marco Rusconi, Giovanni Ghigo, Annamaria Deagostino
Abstract
Abstract Here we present a catalyst‐free protocol for the purple light‐mediated anti ‐Markovnikov functionalization of alkenes with thiols. Crucial to the generation of the thiyl radical was the formation of a key photo‐active complex. More than 30 thioether products were obtained, demonstrating tolerance towards different functional groups and scalability up to 5 mmol of alkene. Two different reaction conditions have been developed, varying both the solvent and the amount of thiol. Depending on the alkene structure, water can be used as an alternative to dichloromethane as a solvent, thus increasing the sustainability of the whole process.
Topics & Concepts
AlkeneChemistryMarkovnikov's ruleThioetherDichloromethaneThiolCatalysisEne reactionSolventPhotochemistryCombinatorial chemistryOrganic chemistryRegioselectivitySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods