Organic Chemistry

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

Authors

Abstract

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.

Content

Thumbnail image of Fumito Chemrxiv Sulfenate 15.09.22_fs.pdf

Supplementary material

Thumbnail image of Fumito Sulfenate Supporting 02.09.22_fs.pdf
Supporting Information
Experimental procedures, Characterization data, Spectra