Brønsted Acid-Catalyzed Regioselective Hydrothiolation of Dienes: Solvent-Controlled Divergent Synthesis of Sulfides
Kai Ji, Ka Lu, Jie Huang, Zi-Hao Li, Hua Ke, Zhi‐Min Chen
Abstract
A Brønsted acid-catalyzed 1,4-addition hydrothiolation of branched 1,3-dienes was explored for the first time. A solvent-controlled divergent synthesis of sulfides is also disclosed. Use of acetonitrile as a solvent gave allylic sulfides as hydrothiolation products, while thiochromane derivatives (hydrothiolation/Friedel-Crafts products) were obtained using dichloromethane as the solvent. The origin of the regioselectivity of hydrothiolation was explored through density functional theory calculations.
Topics & Concepts
RegioselectivityChemistryDichloromethaneSolventCatalysisAcetonitrileOrganic chemistryFriedel–Crafts reactionAllylic rearrangementCombinatorial chemistrySulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsCatalytic C–H Functionalization Methods