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

18 October 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


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.


aryl sulfides
diaryliodonium salts
hypervalent iodine
synthetic methodology
DFT calculations
metal-free reactions

Supplementary materials

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


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