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Issue 3, 2017

Direct thiocyanation of ketene dithioacetals under transition-metal-free conditions

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Abstract

The first direct thiocyanation of ketene dithioacetals has been accomplished in the presence of N-chlorosuccinimide (NCS) and NH4SCN under transition-metal-free conditions. The operationally simple one-pot procedure, which is insensitive to air, was found to be well-tolerated by a wide range of substrates. Terminal alkenes and hydrazine were identified to be qualified candidates for the process as well. Furthermore, the product could be successfully transformed into synthetically and biologically interesting –SCF3 substituted N-heteroaromatic compounds and thiotetrazole containing compounds.

Graphical abstract: Direct thiocyanation of ketene dithioacetals under transition-metal-free conditions

Supplementary files

Article information


Submitted
01 Nov 2016
Accepted
09 Dec 2016
First published
12 Dec 2016

Org. Chem. Front., 2017,4, 369-372
Article type
Research Article

Direct thiocyanation of ketene dithioacetals under transition-metal-free conditions

Q. Chen, Y. Lei, Y. Wang, C. Wang, Y. Wang, Z. Xu, H. Wang and R. Wang, Org. Chem. Front., 2017, 4, 369 DOI: 10.1039/C6QO00676K

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