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Visible-Light-Driven Sulfonation of α-Trifluoromethylstyrenes: Access to Densely Functionalized CF<sub>3</sub>-Substituted Tertiary Alcohol

Yixuan Chen, Zhujun Wang, Jun‐An Xiao, Kai Chen, Hao‐Yue Xiang, Hua Yang

2021Organic Letters57 citationsDOI

Abstract

Reported herein is a visible-light-induced sulfonation of α-trifluoromethylstyrenes with sodium sulfinates, which provides a series of α-trifluoromethyl-β-sulfonyl tertiary alcohols. This new synthetic protocol is enabled by a charge-transfer complex between oxygen and sulfinates, featuring broad substrate scope and scalability. Excellent functional group compatibility and chemoselectivity render this method suitable for sulfonation of pharmaceutically relevant molecules. In the presence of D2O, deuteriotrifluorinated products were also obtained, further demonstrating the flexibility and synthetic potentials of this strategy.

Topics & Concepts

ChemistryChemoselectivityTertiary alcoholsAlcoholCombinatorial chemistryTrifluoromethylSulfonylMoleculeVisible spectrumOrganic chemistryCatalysisAlkylOptoelectronicsPhysicsSulfur-Based Synthesis TechniquesFluorine in Organic ChemistryRadical Photochemical Reactions