Unknown

Dataset Information

0

Pseudocyclic Arylbenziodoxaboroles as Water-Triggered Aryne Precursors in Reactions with Organic Sulfides.

ABSTRACT: 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.

SUBMITTER: Yoshimura A 

PROVIDER: S-EPMC10928713 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Pseudocyclic Arylbenziodoxaboroles as Water-Triggered Aryne Precursors in Reactions with Organic Sulfides.

Yoshimura Akira A   Ngo Kim K   Mironova Irina A IA   Gardner Zachary S ZS   Rohde Gregory T GT   Ogura Nami N   Ueki Akiharu A   Yusubov Mekhman S MS   Saito Akio A   Zhdankin Viktor V VV  

Organic letters 20240226 9

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<sub>2</sub>, CHO, and cyclopropyl) in the aromatic ring or alkyl group of the sulfide. Similar reactions of sulfoxides afford <i>o</i>-hydroxy-substituted sulfonium salts. The structures of key products were confirmed by X-ray analysis. ...[more]

Similar Datasets

Unknown Ligand-Induced Regioselectivity in Metal-Catalyzed Aryne Reactions Using Borylaryl Triflates as Aryne Precursors.
| S-EPMC11527396 | biostudies-literature
Unknown Aryne cycloaddition reactions of benzodioxasilines as aryne precursors generated by catalytic reductive <i>ortho</i>-C-H silylation of phenols with traceless acetal directing groups.
| S-EPMC5501486 | biostudies-literature
Unknown Exploring Possible Surrogates for Kobayashi's Aryne Precursors.
| S-EPMC7017410 | biostudies-literature
Unknown Silylaryl Halides Can Replace Triflates as Aryne Precursors.
| S-EPMC5020908 | biostudies-literature
Unknown The role of aryne distortions, steric effects, and charges in regioselectivities of aryne reactions.
| S-EPMC4221504 | biostudies-literature
Unknown Annulative coupling of vinylboronic esters: aryne-triggered 1,2-metallate rearrangement.
| S-EPMC9400639 | biostudies-literature
Unknown pH-Triggered Removal of Nitrogenous Organic Micropollutants from Water by Using Metal-Organic Polyhedra.
| S-EPMC9322004 | biostudies-literature
Unknown Reactions of HDDA-Derived Benzynes with Sulfides: Mechanism, Modes, and Three-Component Reactions.
| S-EPMC5136460 | biostudies-literature
Unknown Regioselective reactions of 3,4-pyridynes enabled by the aryne distortion model.
| S-EPMC3531798 | biostudies-literature
Unknown Porous Organic Polymers as Fire-Resistant Additives and Precursors for Hyperporous Carbon towards Oxygen Reduction Reactions.
| S-EPMC7239271 | biostudies-literature