N‑Thiocyanatosaccharin: A “Sweet” Electrophilic Thiocyanation Reagent and the Synthetic Applications

N-Thiocyanatosaccharin (R 1 ) was readily prepared from the sweet additive Saccharin in two steps with a 71% overall yield. By applying this new reagent to diverse nucleophiles such as benzothiophenes, indoles, oxindoles, aromatic amines, phenols, β-keto carbonyl compounds, and aromatic ketones, a n...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-02, Vol.83 (3), p.1576-1583
Main Authors: Wu, Di, Qiu, Jiashen, Karmaker, Pran Gopal, Yin, Hongquan, Chen, Fu-Xue
Format: Article
Language:English
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Summary:N-Thiocyanatosaccharin (R 1 ) was readily prepared from the sweet additive Saccharin in two steps with a 71% overall yield. By applying this new reagent to diverse nucleophiles such as benzothiophenes, indoles, oxindoles, aromatic amines, phenols, β-keto carbonyl compounds, and aromatic ketones, a novel electrophilic thiocyanation reaction was achieved with high yields (up to 99%). The potential recycling of Saccharin, the wide scope of substrates, and the mild reaction conditions made this protocol much more practical.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02850