Organic Chemistry

Synthesis of Aryl Sulfides by Metal-Free Arylation of Thiols with Diaryliodonium Salts

Authors

Abstract

Metal-free arylation of thiols with diaryliodonium salts has been developed. The application of a strong organic base ena-bles the C–S bond formation under mild and experimentally simple conditions. The method allows for the synthesis of aryl sulfides containing a broad range of aryl groups from an array of thiols, including aryl, heteroaryl, and alkyl ones. The mechanism of the reaction was studied by DFT calculations, demonstrating that is follows the inner sphere pathway involv-ing the incipient formation of Ar2I(SR) intermediate, followed by the reductive elimination.

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Supplementary material

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Supporting information
experimental procedures, characterization data and copies of NMR spectra for products, computational details and data