Synthesis of Multisubstituted Benzenes from Phenols via Multisubstituted Benzynes

Author:

Yoshida Suguru1,Nagai Akira2,Kobayashi Akihiro21,Sakata Yuki2,Minami Yasunori2,Uchida Keisuke2,Hosoya Takamitsu2ORCID

Affiliation:

1. Department of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science

2. Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU)

Abstract

AbstractA 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.

Funder

Japan Society for the Promotion of Science

Uehara Memorial Foundation

Japan Agency for Medical Research and Development

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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