Abstract
A mild and efficient method for the conversion of alkyl and aryl amines to isothiocyanates via dithiocarbamates has been developed using (CH3)2CO-CS2 as co-solvent and triphosgene as dehydrosulfurization reagent. High yields, mild reaction conditions and excellent functional group compatibility make it become a versatile synthetic method for the preparation of isothiocyanates compared with reported methods.
[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]
GRAPHICAL ABSTRACT
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ACKNOWLEDGMENTS
This work was financially supported by the National Natural Science Foundation of China (21272071), the National Basic Research Program of China (973 Program, 2010CB126100), and the National High Technology Research and Development Program of China (863 Program, 2011AA10A207). This work was also partly supported by the National Key Technology R&D Program of China (2011BAE06B01), Shanghai Leading Academic Discipline Project Project No. B507, and the Fundamental Research Funds for the Central Universities and Special Fund for Agro-scientific Research in the Public Interest (201103007).
Notes
a Reagents and conditions: amine (3 mmol), DABCO (9 mmol), CS2 (15 mL), (CH3)2CO (3 mL), BTC (1 mmol).
b Yield of isolated product.