A general and facile one-pot process of isothiocyanates from amines under aqueous conditions

A general and facile one-pot protocol for the preparation of a broad range of alkyl and aryl isothiocyanates has been developed from their corresponding primary amines under aqueous conditions. This synthetic process involves an in situ generation of a dithiocarbamate salt from the amine substrate b...

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Autores principales: Sun, Nan, Li, Bin, Shao, Jianping, Mo, Weimin, Hu, Baoxiang, Shen, Zhenlu, Hu, Xinquan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3302099/
https://www.ncbi.nlm.nih.gov/pubmed/22423272
http://dx.doi.org/10.3762/bjoc.8.6
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author Sun, Nan
Li, Bin
Shao, Jianping
Mo, Weimin
Hu, Baoxiang
Shen, Zhenlu
Hu, Xinquan
author_facet Sun, Nan
Li, Bin
Shao, Jianping
Mo, Weimin
Hu, Baoxiang
Shen, Zhenlu
Hu, Xinquan
author_sort Sun, Nan
collection PubMed
description A general and facile one-pot protocol for the preparation of a broad range of alkyl and aryl isothiocyanates has been developed from their corresponding primary amines under aqueous conditions. This synthetic process involves an in situ generation of a dithiocarbamate salt from the amine substrate by reacting with CS(2) followed by elimination to form the isothiocyanate product with cyanuric acid as the desulfurylation reagent. The choice of solvent is of decisive importance for the successful formation of the dithiocarbamate salt particularly for highly electron-deficient substrates. This novel and economical method is suitable for scale-up activities.
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spelling pubmed-33020992012-03-15 A general and facile one-pot process of isothiocyanates from amines under aqueous conditions Sun, Nan Li, Bin Shao, Jianping Mo, Weimin Hu, Baoxiang Shen, Zhenlu Hu, Xinquan Beilstein J Org Chem Full Research Paper A general and facile one-pot protocol for the preparation of a broad range of alkyl and aryl isothiocyanates has been developed from their corresponding primary amines under aqueous conditions. This synthetic process involves an in situ generation of a dithiocarbamate salt from the amine substrate by reacting with CS(2) followed by elimination to form the isothiocyanate product with cyanuric acid as the desulfurylation reagent. The choice of solvent is of decisive importance for the successful formation of the dithiocarbamate salt particularly for highly electron-deficient substrates. This novel and economical method is suitable for scale-up activities. Beilstein-Institut 2012-01-10 /pmc/articles/PMC3302099/ /pubmed/22423272 http://dx.doi.org/10.3762/bjoc.8.6 Text en Copyright © 2012, Sun et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Sun, Nan
Li, Bin
Shao, Jianping
Mo, Weimin
Hu, Baoxiang
Shen, Zhenlu
Hu, Xinquan
A general and facile one-pot process of isothiocyanates from amines under aqueous conditions
title A general and facile one-pot process of isothiocyanates from amines under aqueous conditions
title_full A general and facile one-pot process of isothiocyanates from amines under aqueous conditions
title_fullStr A general and facile one-pot process of isothiocyanates from amines under aqueous conditions
title_full_unstemmed A general and facile one-pot process of isothiocyanates from amines under aqueous conditions
title_short A general and facile one-pot process of isothiocyanates from amines under aqueous conditions
title_sort general and facile one-pot process of isothiocyanates from amines under aqueous conditions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3302099/
https://www.ncbi.nlm.nih.gov/pubmed/22423272
http://dx.doi.org/10.3762/bjoc.8.6
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