N-Thiocyanato-dibenzenesulfonimide: a new electrophilic thiocyanating reagent with enhanced reactivity

A novel electrophilic thiocyanating reagent, N-thiocyanato-dibenzenesulfonimide, was prepared and exhibited enhanced electrophilicity with a wide scope of substrates. Thus, it reacted with activated aromatics such as phenols, indoles, anilines and anisoles without a catalyst giving the corresponding...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-08, Vol.17 (30), p.7131-7134
Main Authors: Li, Chengqiu, Long, Pingliang, Wu, Haopeng, Yin, Hongquan, Chen, Fu-Xue
Format: Article
Language:English
Subjects:
Alkenes
Aromatic compounds
Catalysis
Catalysts
Crystallography
Indoles
Ketones
NMR
Nuclear magnetic resonance
Phenols
Reagents
Styrenes
Substrates
Thiocyanates
Zinc
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Summary:A novel electrophilic thiocyanating reagent, N-thiocyanato-dibenzenesulfonimide, was prepared and exhibited enhanced electrophilicity with a wide scope of substrates. Thus, it reacted with activated aromatics such as phenols, indoles, anilines and anisoles without a catalyst giving the corresponding thicyanate derivatives in high yields, while TfOH for unactivated arenes and hetero aromatics and Zn(OTf) for ketones was used as the catalyst, respectively. It is noteworthy that internal alkenes and styrenes were bifunctionalized giving 1,2-amino thiocyanates in high yields.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01340g