Synthesis of Multisubstituted Benzenes from Phenols via Multisubstituted Benzynes

Akira Nagai; Akihiro Kobayashi; Yuki Sakata; Yasunori Minami; Keisuke Uchida; Takamitsu Hosoya; Suguru Yoshida

doi:10.1055/a-1834-2927

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(22): 5017-5025
DOI: 10.1055/a-1834-2927

special topic

Aryne Chemistry in Synthesis

Synthesis of Multisubstituted Benzenes from Phenols via Multisubstituted Benzynes

Akira Nagai

^aLaboratory 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

^aLaboratory 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

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

,

Yuki Sakata

^aLaboratory 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

,

Yasunori Minami

^aLaboratory 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

,

Keisuke Uchida

^aLaboratory 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

^aLaboratory 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∗

^bDepartment 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

A new method to synthesize multifunctionalized arenes from simple phenols through aryne intermediates is described. Multisubstituted aryne precursors were prepared from phenols by Ir-catalyzed C–H borylation, deborylthiolation, O-triflylation, S-oxidation, and further modification through ortho-deprotonation directed by the sulfoxide moiety. Various multisubstituted arenes were synthesized by transformations of highly functionalized aryne intermediates generated from the o-sulfinylaryl triflates.

Key words

aryne intermediates - sulfoxides - Knochel–Hauser base - Grignard reagents - triazoles

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Referenzen

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