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Azido-difluoromethylthiolation of Alkenes with TMSN<sub>3</sub> and PhSO<sub>2</sub>SCF<sub>2</sub>H

Yun‐Tao Shen, Yu‐Song Ran, Bo Jiang, Cui Zhang, Wei Jiang, Ya‐Min Li

2023Organic Letters12 citationsDOI

Abstract

An oxidative azido-difluoromethylthiolation of alkenes by employing TMSN 3 as the azide source and PhSO 2 SCF 2 H as the difluoromethylthiolation reagent is reported. The present method is characterized by good functional group tolerance, broad substrate scope, and short reaction time, thereby providing an efficient access to synthetically useful β-difluoromethylthiolated azides. Mechanistic studies indicate a radical pathway involved in the reaction.

Topics & Concepts

ChemistryReagentAzideScope (computer science)Functional groupSubstrate (aquarium)Oxidative phosphorylationRadicalCombinatorial chemistryReaction conditionsOrganic chemistryCatalysisComputer scienceBiochemistryProgramming languagePolymerGeologyOceanographyFluorine in Organic ChemistrySulfur-Based Synthesis Techniques
Azido-difluoromethylthiolation of Alkenes with TMSN<sub>3</sub> and PhSO<sub>2</sub>SCF<sub>2</sub>H | Litcius