Benzyl Deuteriodifluoromethyl Sulfoxide: An Easily Accessible and Stable Reagent for Direct Deuterodifluoromethylthiolation
Wen Liu, Huilin Lan, Jia-Bo Huang, Wenting Liu, Kezhi Jiang, Xu‐Qiong Xiao, Shao‐Fei Ni, Jingsong Liu, Ying Bai, Xinxin Shao
Abstract
A new, stable and scalable reagent based on a sulfoxide skeleton for direct deuteriodifluoromethylthiolation has been developed. The reagent displays excellent reactivities toward Tf 2 O promoted C–H deuteriodifluoromethylthiolation of electron-rich arenes, indoles, alkenes, and intramolecular lactonization of 2-alkynylbenzoates. Moreover, high deuteration rates and good to excellent yields were achieved under metal-free reaction conditions. As a result, a wide range of deuteriodifluoromethylthilolated compounds were prepared, enabling further applications in drug discovery.
Topics & Concepts
ReagentChemistryIntramolecular forceSulfoxideCombinatorial chemistryDimethyl sulfoxideOrganic chemistryFluorine in Organic ChemistryChemical Reactions and IsotopesInorganic Fluorides and Related Compounds