Pseudocyclic Arylbenziodoxaboroles as Water-Triggered Aryne Precursors in Reactions with Organic Sulfides
Pseudocyclic Arylbenziodoxaboroles as Water-Triggered Aryne Precursors in Reactions with Organic Sulfides
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DOI：
10.1021/acs.orglett.4c00197
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发表时间：
2024-02
期刊：
影响因子：
5.2
通讯作者：
A. Yoshimura;Kim Ngo;I. Mironova;Zachary S Gardner;Gregory T. Rohde;Nami Ogura;Akiharu Ueki;M. Yusubov;Akio Saito;V. Zhdankin
中科院分区：
文献类型：
--
作者：
A. Yoshimura;Kim Ngo;I. Mironova;Zachary S Gardner;Gregory T. Rohde;Nami Ogura;Akiharu Ueki;M. Yusubov;Akio Saito;V. Zhdankin
假环芳基苯并碘杂硼杂环戊烯是一种独特的芳炔前体，在中性水溶液条件下可选择性地与有机硫化物反应，形成相应的锍盐。该反应与硫化物的芳环或烷基中的各种取代基（烷基、卤素、CN、NO2、CHO和环丙基）相容。亚砜的类似反应得到邻羟基取代的锍盐。关键产物的结构经X射线衍射分析确证。
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, NO2, CHO, and cyclopropyl) in the aromatic ring or alkyl group of the sulfide. Similar reactions of sulfoxides afford o-hydroxy-substituted sulfonium salts. The structures of key products were confirmed by X-ray analysis.