Synthesis of Secondary Amides from Thiocarbamates

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

Research output: Contribution to JournalArticleAcademicpeer-review

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 languageEnglish
Pages (from-to)4235-4239
Number of pages5
JournalOrganic Letters
Volume20
Issue number14
Early online date5 Jul 2018
DOIs
Publication statusPublished - 20 Jul 2018

Fingerprint

Thiocarbamates
Amides
amides
disulfides
synthesis
Recycling
recycling
seats
preparation
diphenyl disulfide

Cite this

Mampuys, Pieter ; Ruijter, Eelco ; Orru, Romano V.A. ; Maes, Bert U.W. / Synthesis of Secondary Amides from Thiocarbamates. In: Organic Letters. 2018 ; Vol. 20, No. 14. pp. 4235-4239.
@article{1a8cb931fed6435e9efd86ae4ab0f2cb,
title = "Synthesis of Secondary Amides from Thiocarbamates",
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.",
author = "Pieter Mampuys and Eelco Ruijter and Orru, {Romano V.A.} and Maes, {Bert U.W.}",
year = "2018",
month = "7",
day = "20",
doi = "10.1021/acs.orglett.8b01654",
language = "English",
volume = "20",
pages = "4235--4239",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "14",

}

Synthesis of Secondary Amides from Thiocarbamates. / Mampuys, Pieter; Ruijter, Eelco; Orru, Romano V.A.; Maes, Bert U.W.

In: Organic Letters, Vol. 20, No. 14, 20.07.2018, p. 4235-4239.

Research output: Contribution to JournalArticleAcademicpeer-review

TY - JOUR

T1 - Synthesis of Secondary Amides from Thiocarbamates

AU - Mampuys, Pieter

AU - Ruijter, Eelco

AU - Orru, Romano V.A.

AU - Maes, Bert U.W.

PY - 2018/7/20

Y1 - 2018/7/20

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=85050205399&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85050205399&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.8b01654

DO - 10.1021/acs.orglett.8b01654

M3 - Article

VL - 20

SP - 4235

EP - 4239

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 14

ER -