Palladium-catalyzed intermolecular transthioetherification of aryl halides with thioethers and thioesters.

Yahui Li,Xiao-Feng Wu,Gao Bao

doi:10.1039/c9sc05532k

Abstract

Functional group transfer reactions are an important synthetic tool in modern organic synthesis. Herein, we developed a new palladium-catalyzed intermolecular transthioetherification reaction of aryl halides with thioethers and thioesters. The synthetic utility and practicality of this catalytic protocol are demonstrated in a wide range of successful transformations (>70 examples). This catalytic protocol is applicable in carbonylative coupling processes as well, and the first example of carbonylative methylthioesterification of aryl halides has been achieved. Notably, this work also provides an approach to using natural products, such as methionine and selenomethionine, as the functional group sources.

Highlights

All publication charges for this article have been paid for by the Royal Society of Chemistry
This catalytic protocol is applicable in carbonylative coupling processes as well, and the first example of carbonylative methylthioesterification of aryl halides has been achieved
Functional group transfer reactions have become an indispensable tool in organic synthesis.[1]

Summary

Introduction

All publication charges for this article have been paid for by the Royal Society of Chemistry. Functional group transfer reactions are an important synthetic tool in modern organic synthesis. We developed a new palladium-catalyzed intermolecular transthioetherification reaction of aryl halides with thioethers and thioesters. We wish to report here the rst example of palladium-catalyzed thiomethylation and carbonylative thiomethylation of an aryl halide by using an alkyl sul de or methyl thioester as a convenient methylthiolating reagent (Fig. 1D).

Results

Conclusion