A General and Facile One-Pot Process of Isothiocyanates from Amines under Aqueous Conditions
News Aug 21, 2012
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.
University of Wisconsin–Madison Professor of Chemistry Shannon Stahl has received the Steenbock Professorship in Chemical Sciences. In addition to advancing the fundamental science in this area, Stahl has been involved in numerous industrial collaborations that have led to practical applications, including target applications relevant to pharmaceutical synthesis.READ MORE