KCN和NaOCl·5H2O在双相体系中合成芳基和烷基磺酰氰化物。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-10-15 DOI:10.1021/acs.joc.5c02290

Atsushi Baba,Yutaro Nakamura,Tsuyoshi Matsuzaki,Takeyuki Suzuki,Masaru Kondo,Ryo Takita

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引用次数: 0

摘要

在弱酸性条件下，以氰化钾（KCN）和五水次氯酸钠（NaOCl·5H2O）为原料，以亚硫酸钠（R-SO2Na）为原料合成芳基和烷基磺酰氰化物（R-SO2CN）。双相介质对于抑制副反应和包括13c标记衍生物在内的广泛的普遍性是必不可少的。原位生成的氯化氰（ClCN）被实验确定为关键的反应物质。通过电子调谐磺酰氰化物在有用转化中的增强反应性，展示了合成效用。

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Synthesis of Aryl and Alkyl Sulfonyl Cyanides Using KCN and NaOCl·5H2O in a Biphasic System.

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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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.