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A General and Facile One-Pot Process of Isothiocyanates from Amines under Aqueous Conditions

Published: Tuesday, August 21, 2012
Last Updated: Tuesday, August 21, 2012
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This newly developed method has the potential to convert a wide range of primary alkyl and arylamines into their corresponding isothiocyanates in excellent yields and provides promise for further scale-up activities.

Abstract
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.

The article is published online in Beilstein Journal of Organic Chemistry and is free to access.


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