Direct Sulfoxidation of Aromatic Methyl Thioethers with Aryl Halides by Copper-Catalyzed C(sp3)–H Bond Activation

Runsheng Xu,Suli Tong,Yueer Zhu,Feixiang Xiong

doi:10.3390/catal9010105

Runsheng Xu, Suli Tong + Show 2 more

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https://doi.org/10.3390/catal9010105

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Abstract

A copper-catalyzed direct sulfoxidation reaction by C(sp3)–H bond activation has been developed. Starting from sample aromatic methyl thioethers with aryl halides, versatile biologically-active arylbenzylsulfoxide derivatives were efficiently synthesized in good to high yields under mild conditions. This new methodology provides an economical approach toward C(sp3)–C(sp2) bond formation.

Highlights

Starting sample aromatic methyl thioetherswith witharyl aryl halides, halides, versatile biologically-active biologically-active arylbenzylsulfoxide arylbenzylsulfoxide derivatives derivatives were were efficiently efficiently synthesized synthesized in in good to high yields under mild conditions
The results showed that both of the experiments
The results showed that bothcontrol of the elimination step, intermediate generated the desired product of provided benzylsulfoxide the elimination step, intermediate generated the desired product of benzylsulfoxide followed by the reductive copper-catalyzed oxidation in the presence oxygen

Summary

Introduction

Starting sample aromatic methyl thioetherswith witharyl aryl halides, halides, versatile biologically-active biologically-active arylbenzylsulfoxide arylbenzylsulfoxide derivatives derivatives were were efficiently efficiently synthesized synthesized in in good to high yields under mild conditions. 1. Introduction derivatives are the most privileged privileged scaffolds scaffolds in natural natural biological biological products products [1],. The most most common common synthetic syntheticmethod methodfor forbenzylsulfoxide benzylsulfoxidederivatives derivatives is sulfide oxidation, The is sulfide oxidation, as as illustrated in [7]. The strong oxidizing agents and reactive organolithium contribute to illustrated in Scheme 2A [7]. The strong oxidizing agents and reactive organolithium contribute to the wide of this method, its scope limited. Have been the wideuse use of this method, its isscope is Benzylsulfoxides limited.

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Conclusion