Mild and Efficient Preparation of Arylphosphonium and Arylammonium Salts under Aqueous Conditions at Room Temperature Using Pseudocyclic Arylbenziodoxaboroles as Aryne Precursors

Akira Yoshimura; Kristina M. Zvereva; Gunnar Frahm; Irina A. Mironova; Dmitrii M. Noskov; Zachary S. Gardner; Tatsuya Suzuki; Akiharu Ueki; Mekhman S. Yusubov; Akio Saito; Viktor V. Zhdankin

doi:10.1248/cpb.c25-00746

Regular Article

Mild and Efficient Preparation of Arylphosphonium and Arylammonium Salts under Aqueous Conditions at Room Temperature Using Pseudocyclic Arylbenziodoxaboroles as Aryne Precursors

Akira Yoshimura , Kristina M. Zvereva, Gunnar Frahm, Irina A. Mironova, Dmitrii M. Noskov, Zachary S. Gardner, Tatsuya Suzuki, Akiharu Ueki, Mekhman S. Yusubov, Akio Saito, Viktor V. Zhdankin

Author information

Akira Yoshimura Corresponding author
Faculty of Pharmaceutical Sciences, Aomori University, 2–3–1 Kobata, Aomori 030–0943, Japan
Kristina M. Zvereva
Research School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, Lenina av., 30, Tomsk 634050, Russia
Gunnar Frahm
Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, U.S.A.
Irina A. Mironova
Research School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, Lenina av., 30, Tomsk 634050, Russia
Dmitrii M. Noskov
Research School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, Lenina av., 30, Tomsk 634050, Russia
Zachary S. Gardner
Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, U.S.A.
Tatsuya Suzuki
Faculty of Pharmaceutical Sciences, Aomori University, 2–3–1 Kobata, Aomori 030–0943, Japan
Akiharu Ueki
Faculty of Pharmaceutical Sciences, Aomori University, 2–3–1 Kobata, Aomori 030–0943, Japan
Mekhman S. Yusubov
Research School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, Lenina av., 30, Tomsk 634050, Russia
Akio Saito
Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2–24–16 Naka-cho, Koganei, Tokyo 184–8588, Japan
Viktor V. Zhdankin Corresponding author
Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, U.S.A.

Keywords: aryne, arylbenziodoxaborole, arylphosphonium salt, arylammonium salt

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Supplementary material

2026 Volume 74 Issue 2 Pages 166-169

DOI https://doi.org/10.1248/cpb.c25-00746

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Abstract

Pseudocyclic arylbenziodoxaboroles are unique aryne precursors under neutral aqueous conditions that selectively react with tertiary organic phosphines or amines at room temperature to form the corresponding aryl-substituted quaternary phosphonium or ammonium salts in high yields. This reaction has been further extended to the preparation of tetraarylarsonium and tetraarylstibonium salts.

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