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

Akira Yoshimura; Kim Ngo; Irina A Mironova; Zachary S Gardner; Gregory T Rohde; Nami Ogura; Akiharu Ueki; Mekhman S Yusubov; Akio Saito; Viktor V Zhdankin

doi:10.1021/acs.orglett.4c00197

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

Org Lett. 2024 Mar 8;26(9):1891-1895. doi: 10.1021/acs.orglett.4c00197. Epub 2024 Feb 26.

Authors

Affiliations

¹ Faculty of Pharmaceutical Sciences, Aomori University, 2-3-1 Kobata, Aomori 030-0943, Japan.
² Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, Minnesota 55812, United States.
³ Research School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, Lenina av., 30, 634050 Tomsk, Russia.
⁴ Marshall School, Duluth, Minnesota 55811, United States.
⁵ Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan.

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.