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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Research output: Contribution to Journal › Article › Academic › peer-review

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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
Research Foundation-Flanders
Fonds Wetenschappelijk Onderzoek
Universiteit Antwerpen
Herculesstichting

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 6 Clean Water and Sanitation
SDG 12 Responsible Consumption and Production

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

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AU - Ruijter, Eelco

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AB - 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.

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Synthesis of Secondary Amides from Thiocarbamates

Abstract

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UN SDGs

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