Synthesis of Secondary Amides from Thiocarbamates [component]

The synthesis of secondary amides from readily accessible and bench-stable substituted Sphenyl thiocarbamates and Grignard reactants is reported. Oxidative workup allows recycling of the thiolate leaving group as diphenyl disulfide. Diphenyl disulfide can be transformed into S-phenyl benzenethiosulfonate, a reactant required for thiocarbamate synthesis. This amide synthesis is suitable for the preparation of challenging amides, which are not or hardly accessible via classical approaches.
doi:10.1021/acs.orglett.8b01654.s001 fatcat:pjpciyymnnachbpkpyq3gyotsu