Yoshimura Akira, Ngo Kim, Mironova Irina A, Gardner Zachary S, Rohde Gregory T, Ogura Nami, Ueki Akiharu, Yusubov Mekhman S, Saito Akio, Zhdankin Viktor V
Faculty of Pharmaceutical Sciences, Aomori University, 2-3-1 Kobata, Aomori 030-0943, Japan.
Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, Minnesota 55812, United States.
Org Lett. 2024 Mar 8;26(9):1891-1895. doi: 10.1021/acs.orglett.4c00197. Epub 2024 Feb 26.
Pseudocyclic arylbenziodoxaboroles are unique aryne precursors under neutral aqueous conditions that selectively react with organic sulfides, forming the corresponding sulfonium salts. This reaction is compatible with various substituents (alkyl, halogen, CN, NO, CHO, and cyclopropyl) in the aromatic ring or alkyl group of the sulfide. Similar reactions of sulfoxides afford -hydroxy-substituted sulfonium salts. The structures of key products were confirmed by X-ray analysis.
伪环芳基苯并碘硼杂环戊烷是在中性水条件下独特的芳炔前体，可与有机硫化物选择性反应，形成相应的锍盐。该反应与硫化物芳环或烷基中的各种取代基（烷基、卤素、CN、NO、CHO和环丙基）兼容。亚砜的类似反应可得到β-羟基取代的锍盐。关键产物的结构通过X射线分析得以确证。
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