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Updated: Jan 15, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Synthesis of Aryl and Alkyl Sulfonyl Cyanides Using KCN and NaOCl·5H2O in a Biphasic System
Atsushi Baba1, Yutaro Nakamura1, Tsuyoshi Matsuzaki2
1School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
Abstract:
An efficient and practical protocol has been developed for synthesizing aryl and alkyl sulfonyl cyanides (R-SO2CN) from sodium sulfinates (R-SO2Na) by employing potassium cyanide (KCN) and sodium hypochlorite pentahydrate (NaOCl·5H2O) under weakly acidic conditions. A biphasic medium is essential for suppressing side reactions and enabling broad generality including 13C-labeled derivatives. In situ-generated cyanogen chloride (ClCN) was identified experimentally as the key reactive species. The synthetic utility is showcased through the enhanced reactivity of electronically tuned sulfonyl cyanides in useful transformations.
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