One-Pot Generation of Functionalized Benzynes from Readily Available 2‑Hydroxyphenylboronic Acids

We developed a one-pot method for the generation of benzynes from a range of readily available 2-hydroxyphenylboronic acids. This method features the in situ activation of both boronic acid and hydroxyl groups of the substrate to enhance benzyne generation at 60 °C. Such mild conditions facilitate t...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-03, Vol.85 (5), p.3383-3392
Main Authors: Ikawa, Takashi, Sun, JingKai, Takagi, Akira, Akai, Shuji
Format: Article
Language:English
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Summary:We developed a one-pot method for the generation of benzynes from a range of readily available 2-hydroxyphenylboronic acids. This method features the in situ activation of both boronic acid and hydroxyl groups of the substrate to enhance benzyne generation at 60 °C. Such mild conditions facilitate the generation of functionalized benzynes that immediately react with diverse arynophiles to produce multisubstituted fused benzenes.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b03169