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Mampuys P, Ruijter E, Orru RVA, et al. Synthesis of Secondary Amides from Thiocarbamates. Org Lett. 2018;20(14):4235-4239doi: 10.1021/acs.orglett.8b01654.
Mampuys, P., Ruijter, E., Orru, R. V. A., & Maes, B. U. W. (2018). Synthesis of Secondary Amides from Thiocarbamates. Organic letters, 20(14), 4235-4239. https://doi.org/10.1021/acs.orglett.8b01654
Mampuys, Pieter, et al. "Synthesis of Secondary Amides from Thiocarbamates." Organic letters vol. 20,14 (2018): 4235-4239. doi: https://doi.org/10.1021/acs.orglett.8b01654
Mampuys P, Ruijter E, Orru RVA, Maes BUW. Synthesis of Secondary Amides from Thiocarbamates. Org Lett. 2018 Jul 20;20(14):4235-4239. doi: 10.1021/acs.orglett.8b01654. Epub 2018 Jul 05. PMID: 29975068.
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Org Lett. 2018 Jul 20;20(14):4235-4239. doi: 10.1021/acs.orglett.8b01654. Epub 2018 Jul 05.

Synthesis of Secondary Amides from Thiocarbamates.

Organic letters

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

Affiliations

  1. Organic Synthesis, Department of Chemistry , University of Antwerp , Groenenborgerlaan 171 , 2020 Antwerp , Belgium.
  2. Department of Chemistry and Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines and Systems (AIMMS) , Vrije Universiteit Amsterdam , De Boelelaan 1108 , 1081 HZ Amsterdam , The Netherlands.

PMID: 29975068 DOI: 10.1021/acs.orglett.8b01654

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.

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