Litcius/Paper detail

Arylthianthrenium Salts as the Aryl Sources: Visible Light/Copper Catalysis-Enabled Intermolecular Azidosulfonylation of Alkenes

Hao Xu, Xufeng Li, Yifei Wang, Xiuyan Song, Yongjia Shi, Jian Lv, Daoshan Yang

2024Organic Letters51 citationsDOI

Abstract

The difunctionalization of alkenes using aryl thianthrenium salts as the aryl sources has been reported sporadically. However, the four-component difunctionalization of alkenes on the basis of aryl thianthrenium salts has not been reported thus far and still remains a challenge. Herein, a visible light/copper catalysis-enabled four-component reaction of aryl thianthrenium salts, DABCO·(SO 2 ) 2, alkenes, and TMSN 3 is presented, which affords a facile approach to β-azidosulfones in good yields with broad substrate scope and excellent functional group tolerance. This strategy indirectly realizes the method for the synthesis of β-azidosulfones through site-selective aryl C–H bond functionalization and alkene difunctionalization. This developed method is an important complement to thianthrenium salts chemistry.

Topics & Concepts

ChemistryArylIntermolecular forceCopperCatalysisPhotochemistryVisible spectrumCombinatorial chemistryMoleculeOrganic chemistryAlkylOptoelectronicsPhysicsSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods