Synthesis of Secondary Amides from Thiocarbamates

Pieter Mampuys; Eelco Ruijter; Romano V.A. Orru; Bert U.W. Maes

doi:10.1021/acs.orglett.8b01654

Synthesis of Secondary Amides from Thiocarbamates

Pieter Mampuys, Eelco Ruijter, Romano V.A. Orru, Bert U.W. Maes^*

^*Corresponding author for this work

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Abstract

The synthesis of secondary amides from readily accessible and bench-stable substituted S-phenyl 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 that are not or hardly accessible via classical approaches.

Original language	English
Pages (from-to)	4235-4239
Number of pages	5
Journal	Organic letters
Volume	20
Issue number	14
Early online date	5 Jul 2018
DOIs	https://doi.org/10.1021/acs.orglett.8b01654
Publication status	Published - 20 Jul 2018

Funding

This research was financially supported by the University of Antwerp (BOF, IOF), the Research Foundation-Flanders (FWO) (Ph.D. fellowship to P.M., research project and WOG), and the Hercules Foundation. The authors thank Prof. Christophe Vande Velde (University of Antwerp) for thermogravimetric analysis.

Funders	Funder number
Research Foundation-Flanders
Fonds Wetenschappelijk Onderzoek
Universiteit Antwerpen
Herculesstichting

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Synthesis of Secondary Amides from ThiocarbamatesFinal published version, 637 KBLicence: Article 25fa Dutch Copyright Act

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AU - Maes, Bert U.W.

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Synthesis of Secondary Amides from Thiocarbamates

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