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 correspondin...

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Published inOrganic & biomolecular chemistry Vol. 17; no. 3; pp. 7131 - 7134
Main Authors Li, Chengqiu, Long, Pingliang, Wu, Haopeng, Yin, Hongquan, Chen, Fu-Xue
Format Journal Article
LanguageEnglish
Published 31.07.2019
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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) 2 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. N -Thiocyanato-dibenzenesulfonimide: a new electrophilic thiocyanating reagent was readily prepared and exhibited enhanced reactivity with a wide scope of substrates.
Bibliography:1919695
For ESI and crystallographic data in CIF or other electronic format see DOI
Electronic supplementary information (ESI) available: Details of reaction procedures, characteristic data of all new compounds, copies of NMR spectra. CCDC
10.1039/c9ob01340g
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01340g