An Efficient Copper-Catalyzed One-Pot Synthesis of Diaryl Thioethers by Coupling of Arylboronic Acids with Potassium Ethyl Xanthogenate under Mild Conditions

Abstract

A simple and environmentally benign one-pot synthesis of diaryl thioethers by coupling of arylboronic acids with potassium ethyl xanthogenate through a double arylation process has been developed. The aryl thiols were generated in situ, and the reactions proceeded smoothly to give the corresponding products in good to excellent yields under very mild conditions.

Eco‐compatible three component strategies for C‐S bond formation in thioether and S‐aryl‐carbamodithioate compounds catalyzed by copper(II) nanoparticles supported on modified AlPO4

“…The use of eco‐compatible, and versatile transition metal (especially copper) catalysts for mild C‐S bond formation reactions have been received too much attention because of their marvelous products with many important biological and pharmaceutical properties . Since the C‐S bond formation is one of the major routes for the synthesis of a wide range of organic compounds, many studies have been reported in this field .…”

“…The use of eco‐compatible, and versatile transition metal (especially copper) catalysts for mild C‐S bond formation reactions have been received too much attention because of their marvelous products with many important biological and pharmaceutical properties . Since the C‐S bond formation is one of the major routes for the synthesis of a wide range of organic compounds, many studies have been reported in this field . The investigation of methods free from foul‐smelling thiols such as using ‘three component reactions for C‐S bond formation’ lead researchers to the develop eco‐compatible and eco‐friendly synthetic approaches …”

“…Since the C‐S bond formation is one of the major routes for the synthesis of a wide range of organic compounds, many studies have been reported in this field . The investigation of methods free from foul‐smelling thiols such as using ‘three component reactions for C‐S bond formation’ lead researchers to the develop eco‐compatible and eco‐friendly synthetic approaches …”

“…Formation of the C‐S bond is relatively problematic due to the parallel oxidative S‐S bond formation and consequently deactivation of metal‐based catalysts by sulphur‐containing compounds. A wide range of transition metals, including Pd, Cu, Co, Ni, and recently Fe catalysts, with suitable ligands, have been used for aryl‐sulfur bond formation. Over the past few decades, Cu(II) complexes have been chosen as possible options to perform the metal catalyzed organic reactions, and many researchers have investigated these types of the complexes in many organic reactions.…”

Copper nanoparticles supported on polyaniline‐functionalized multiwall carbon nanotubes: An efficient and recyclable catalyst for synthesis of unsymmetric sulfides using potassium ethyl xanthogenate in water

“…Recently, thiourea, potassium thiocyanate, thiolates, carbon disulfide, sulfur powder, thioimide, sodium thiosulfate and ethyl xanthogenate have been reported as sulfur sources in C─S bond formation. However, these reactions are often conducted in dimethylformamide (DMF) at a high temperature.…”