N-Thiocyanatosaccharin: A "Sweet" Electrophilic Thiocyanation Reagent and the Synthetic Applications.

J Org Chem

School of Chemistry and Chemical Engineering, Beijing Institute of Technology, No. 5 Zhongguancun Street, Haidian District, Beijing 100081, China.

Published: February 2018

N-Thiocyanatosaccharin (R) 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.

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http://dx.doi.org/10.1021/acs.joc.7b02850DOI Listing

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