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

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 subs...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 4; no. 3; pp. 369 - 372
Main Authors Chen, Qiao, Lei, Yingjie, Wang, Yanfang, Wang, Chao, Wang, Yanan, Xu, Zhaoqing, Wang, Huan, Wang, Rui
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.03.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALKENES
ROUTE
PALLADIUM
THIOCYANOOXYGENATION
FACILE SYNTHESIS
TRIFLUOROMETHYLTHIOCYANATION
C-3 THIOCYANATION
EFFICIENT
ACCESS
ARYL THIOCYANATES
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Summary: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.
ISSN:2052-4129
DOI:10.1039/c6qo00676k