Synthesis of Aryl and Alkyl Sulfonyl Cyanides Using KCN and NaOCl·5H <sub>2</sub> O in a Biphasic System
An efficient and practical protocol has been developed for synthesizing aryl and alkyl sulfonyl cyanides (R-SO<sub>2</sub>CN) from sodium sulfinates (R-SO<sub>2</sub>Na) by employing potassium cyanide (KCN) and sodium hypochlorite pentahydrate (NaOCl·5H<sub>2</sub>O) under weakly acidic conditions. A biphasic medium is essential for suppressing side reactions and enabling broad generality including <sup>13</sup>C-labeled derivatives. <i>In situ</i>-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.
Authors
- Masaru Kondo (ORCID: https://orcid.org/0000-0001-6299-5718)
- Ryo Takita (ORCID: https://orcid.org/0000-0003-4104-9890)
- Tsuyoshi Matsuzaki
- Yutaro Nakamura (ORCID: https://orcid.org/0000-0002-0002-7444)
- Takeyuki Suzuki (ORCID: https://orcid.org/0000-0002-2137-0276)
- Atsushi Baba
Institutions
- University of Shizuoka (JP)
- The University of Osaka (JP)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-10-15
- DOI
- https://doi.org/10.1021/acs.joc.5c02290
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.00