Generation of benzyne from aryl benziodoxaborole triflate under aqueous conditions and its reactions with alkyl aryl sulfides

Bibliographic Details
Parent link:Arkivoc.— .— New-York: ARKAT USA, Inc.
Vol. 1.— 2024.— Article number 202412213, 11 p.
Corporate Author: National Research Tomsk Polytechnic University (570)
Other Authors: Yoshimura A. Akira, Ngo Kim, Mironova I. A. Irina Andreevna, Gardner S. Zachary, Ogura Nami, Ueki Akiharu, Yusubov M. S. Mekhman Suleiman-Ogly (Suleimanovich), Saito Akio, Zhdankin V. V. Viktor Vladimirovich
Summary:Title screen
Mesityl benziodoxaborole triflate is a unique benzyne precursor under aqueous conditions in the presence of NaHCO3 at room temperature. Reactions of alkyl aryl sulfides with benzyne generated under these conditions selectively afford the corresponding sulfonium salts. In contrast, the previously reported reactions of alkyl aryl sulfides with common benzyne precursors under strongly basic anhydrous conditions lead to various products of cyclization, rearrangement, or elimination but not to sulfonium salts. This very mild procedure can be further extended to the preparation of sulfonium salts from diaryl sulfides, dialkyl sulfides, cyclic alkyl and arylsulfides, as well as a selenonium salt from diphenyl selenide.
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Published: 2024
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Online Access:https://doi.org/10.24820/ark.5550190.p012.213
Format: Electronic Book Chapter
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=673457