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

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.