Synthesis of 6<i>H-</i>Benzo[<i>c</i>]chromene Scaffolds from <i>O</i>-Benzylated Phenols through a C–H Sulfenylation/Radical Cyclization Sequence
Steve Karreman, Simon B. H. Karnbrock, Sebastian Kolle, Christopher Golz, Manuel Alcarazo
Abstract
bond. Mechanistic studies reveal that this initial radical species cyclizes following a kinetically favored 5-exo-trig pathway. Subsequent ring expansion, favored by rearomatization, delivers the desired tricyclic systems.
Topics & Concepts
ChemistrySulfoniumRegioselectivityArylPhenolsBond cleavageRing (chemistry)Cleavage (geology)Medicinal chemistryTricyclicAryl radicalRadical ionRadicalStereochemistrySalt (chemistry)Organic chemistryCatalysisIonAlkylEngineeringGeotechnical engineeringFracture (geology)Sulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods