Use of Base Control To Provide High Selectivity between Diaryl Thioether and Diaryl Disulfide for C–S Coupling Reactions of Aryl Halides and Sulfur and a Mechanistic Study
Citations Over TimeTop 10% of 2013 papers
Abstract
Previous studies have reported that S-arylation produces diaryl disulfide when the precursors include sulfur powder and aryl halide using CuI as the catalyst. However, our research has revealed that the use of different bases in the above S-arylation process results in the coproduction of diarylsulfane and diaryldisulfane. In addition, we have demonstrated that the ratio of the two products can be controlled by selecting the alkalinity of the bases. 1H NMR spectra showed that diaryldisulfane was the first product, which became the reagent in a reaction with aryl halide to form diarylsulfane through CuI catalysis. Various aryl halides were tested to enhance the selectivity between diarylsulfane and diaryldisulfane using various different bases, leading to the following principles. A weak base, such as metal carbonate or acetate, results in the production of only diaryldisulfane; a strong base, such as metal hydroxide, results in the production of both diaryldisulfane and diarylsulfane. According to DFT calculations, hydroxide ions, which were exchanged for iodide and bonded with Cu, affected Cu electrons more strongly to reduce diaryl disulfide.
Related Papers
- → Mixed Halide Perovskite Solar Cells. Consequence of Iodide Treatment on Phase Segregation Recovery(2018)107 cited
- → The mechanism of the oxidative addition of aryl halides to Pd-catalysts: a DFT investigation(2004)105 cited
- → Unraveling the Role of Monovalent Halides in Mixed‐Halide Organic–Inorganic Perovskites(2015)13 cited
- → Colorimetric Chemosensor Array for Determination of Halides(2021)12 cited
- → Mutual interference effects during the successive determination of lodide, bromide, chloride and fluoride in a single sample using halide-selective electrodes(1975)7 cited