Facile and Versatile Synthesis of Alkyl and Aryl Isothiocyanates by Using Triphosgene and CoSolvent

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.

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GRAPHICAL ABSTRACT

Keywords:

• Amines
• co-solvent
• dehydrosulfurization
• isothiocyanates
• triphosgene

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.