A Sulfoxide Reagent for One-Pot, Three-Component Syntheses of Sulfoxides and Sulfinamides

19 September 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Sulfoxides and sulfinamides represent versatile sulfur functional groups found in ligands, chiral auxiliaries, and bioactive molecules. However, canonical two-component syntheses relying on substrates with a preinstalled C–S bond impede efficient and modular access to these sulfur motifs. Herein is presented the application of an easily prepared, bench stable sulfoxide reagent for one-pot, three-component syntheses of sulfoxides and sulfinamides. The sulfoxide reagent donates the SO unit upon the reaction with a Grignard reagent (RMgX) as a sulfenate anion (RSO–). While subsequent trapping reactions of this key intermediate with carbon electrophiles provide sulfoxides, a range of tertiary, secondary, and primary sulfinamides can be prepared by substitution reactions with electrophilic amines. The syntheses of sulfinamide analogs of amide- and sulfonamide-containing drugs illustrate the utility of the method for the rapid preparation of medicinally relevant molecules.


synthetic methods
Grignard reaction
one-pot synthesis

Supplementary materials

Supporting Information
Experimental procedures, Characterization data, Spectra


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