3‑Hydroxy-2-(trialkylsilyl)phenyl Triflate: A Benzyne Precursor Triggered via 1,3-C-sp2‑to‑O Silyl Migration

3-Hydroxy-2-(trialkylsilyl)­phenyl triflates are presented as new versatile hydroxyaryne precursors. These are base-activated aryne precursors induced via a C-sp2-to-O 1,3-Brook rearrangement. The reaction of various arynophiles and 3-trialkylsiloxybenzyne generated from 3-hydroxy-2-(trialkylsilyl)­...

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Veröffentlicht in:Organic letters 2017-11, Vol.19 (22), p.6224-6227
Hauptverfasser: Kwon, Yong-Ju, Jeon, Young-Kyo, Sim, Ha-Bin, Oh, In-Young, Shin, Inji, Kim, Won-Suk
Format: Artikel
Sprache:eng
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Zusammenfassung:3-Hydroxy-2-(trialkylsilyl)­phenyl triflates are presented as new versatile hydroxyaryne precursors. These are base-activated aryne precursors induced via a C-sp2-to-O 1,3-Brook rearrangement. The reaction of various arynophiles and 3-trialkylsiloxybenzyne generated from 3-hydroxy-2-(trialkylsilyl)­phenyl triflate efficiently afforded highly regioselective phenol derivatives. Furthermore, through crossover experiments, the intramolecular mechanism of silyl migration was demonstrated.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b03160