Visible-Light-Mediated Divergent and Regioselective Vicinal Difunctionalization of Styrenes with Arylazo Sulfones
Lorenzo Di Terlizzi, Luca Nicchio, Camilla Callegari, Simone Scaringi, Luc Neuville, Maurizio Fagnoni, Stefano Protti, Géraldine Masson
Abstract
Activated by visible light, arylazo sulfones can serve as multifaceted reactants and are employed in diazenylation, sulfonylation, and arylation reactions under (photo)catalyst-free conditions. Such versatile reactivity enabled us to develop an operationally simple, regioselective, and tunable difunctionalization of styrenes with arylazo sulfones to produce α-sulfonyl arylhydrazones and 1,2-alkoxyarylated products in moderate to excellent yields. Furthermore, such difunctionalized products have been exploited as key building blocks for the synthesis of various heterocycles.
Topics & Concepts
RegioselectivityChemistryVicinalReactivity (psychology)SulfonylCombinatorial chemistryCatalysisOrganic chemistryAlternative medicineMedicinePathologyAlkylSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods