Pseudocyclic Arylbenziodoxaboroles as Water-Triggered Aryne Precursors in Reactions with Organic Sulfides
Akira Yoshimura, Kim Ngo, Irina A. Mironova, Zachary Gardner, Gregory T. Rohde, Nami Ogura, Akiharu Ueki, Mekhman S. Yusubov, Akio Saito, Viktor V. Zhdankin
Abstract
High Resolution Image Download MS PowerPoint Slide 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 2, 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.
Topics & Concepts
ChemistryAryneOrganic chemistryCombinatorial chemistryCyclization and Aryne ChemistryChemical Reactions and MechanismsCatalytic Alkyne Reactions