Copper-Catalyzed Redox Coupling of Nitroarenes with Sodium Sulfinates

Saiwen Liu,Ru Chen,Jin Zhang

doi:10.3390/molecules24071407

Abstract

A simple copper-catalyzed redox coupling of sodium sulfinates and nitroarenes is described. In this process, abundant and stable nitroarenes serve as both the nitrogen sources and oxidants, and sodium sulfinates act as both reactants and reductants. A variety of aromatic sulfonamides were obtained in moderate to good yields with broad substrate scope. No external additive is employed for this kind of transformation.

Highlights

Nitroarenes are a class of the most readily available starting materials in synthetic organic chemistry
Aromatic sulfonamides were formed in moderate to good yields in the absence of external oxidant or reductant. Active functional groups such as ester, cyano, and halogens were well tolerated under the optimized conditions. This method affords an alternative route for the synthesis of N-aryl sulfonamides under mild conditions
The detailed mechanism and the synthetic applications of this reaction are currently under investigation

Summary

Introduction

Nitroarenes are a class of the most readily available starting materials in synthetic organic chemistry. There has been significant interest in the transition-metal-catalyzed C-N bond formation from nitroarenes by use of in situ borrowing-hydrogen strategy [14,15,16,17,18,19]. Among these transformations, two types of reactions can be summarized according to the resultant products: reductive cyclizations and reductive couplings. They provide convenient access to amine, amide and N-heterocycles directly from aromatic nitro compounds [20,21,22,23,24,25,26,27,28,29,30,31]

Methods

Results

Conclusion