K2S2O8-mediated regio- and stereo-selective thiocyanation of enamides with NH4SCN

A direct and straightforward thiocyanation of enamides with NH4SCN under metal-free conditions has been accomplished. A variety of (E)-beta-thiocyanoenamides are readily produced in a regio- and stereo-selective manner. The protocol features mild reaction conditions, good functional group tolerance...

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Published inOrganic & biomolecular chemistry Vol. 19; no. 11; pp. 2512 - 2516
Main Authors Gu, Qingyun, Wang, Qiyang, Dai, Wenjing, Wang, Xin, Ban, Yingguo, Liu, Tianqing, Zhao, Yu, Zhang, Yanan, Ling, Yong, Zeng, Xiaobao
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.03.2021
Royal Society of Chemistry
Subjects
Chemical reactions
Chemistry
Chemistry, Organic
Coupling (molecular)
Cross coupling
Crystallography
Functional groups
Palladium
Physical Sciences
Potassium persulfate
Science & Technology
Sulfur
Thiocyanates
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Summary:A direct and straightforward thiocyanation of enamides with NH4SCN under metal-free conditions has been accomplished. A variety of (E)-beta-thiocyanoenamides are readily produced in a regio- and stereo-selective manner. The protocol features mild reaction conditions, good functional group tolerance and operational simplicity. The potential utility of this strategy was further demonstrated by transformation of thiocyanate into thiotetrazole-containing compounds and a Pd-catalyzed cross-coupling reaction to afford six- or seven-membered sulfur-containing heterocycles. Mechanistic insights into the reaction indicate that the reaction may proceed via a radical mechanism.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob00156f