Migrative Thioamination of Aryne Intermediates Generated from o-Iodoaryl Triflates

Shinya Tabata; Mai Minoshima; Akihiro Kobayashi; Takamitsu Hosoya; Suguru Yoshida

doi:10.1055/a-2030-6299

Synlett, Table of Contents

Synlett 2023; 34(11): 1259-1264
DOI: 10.1055/a-2030-6299

letter

Migrative Thioamination of Aryne Intermediates Generated from o-Iodoaryl Triflates

Shinya Tabata

^aDepartment of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan

,

Mai Minoshima

^bLaboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan

,

Akihiro Kobayashi

^aDepartment of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan

^bLaboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan

,

Takamitsu Hosoya

^bLaboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan

,

Suguru Yoshida∗

^aDepartment of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan

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Abstract

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Abstract

Migrative thioamination of aryne intermediates takes place using various o-iodoaryl triflates and sulfilimines. The selective migration realizes the facile synthesis of a broad range of highly functionalized o-thioaminated diaryl sulfides. We succeeded in the ring expansion of cyclic sulfilimines enabling us to prepare eight- and nine-membered organosulfurs from dibenzothiophene- and thianthrene-type sulfilimines, respectively.

Key words

arynes - sulfilimines - diaryl sulfides - thioamination - migration

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References

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