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3-Hydroxy-2-(trialkylsilyl)phenyl Triflate: A Benzyne Precursor Triggered via 1,3-C-sp(2)-to-O Silyl Migration
- 3-Hydroxy-2-(trialkylsilyl)phenyl Triflate: A Benzyne Precursor Triggered via 1,3-C-sp(2)-to-O Silyl Migration
- Kwon, Yong-Ju; Jeon, Young-Kyo; Sim, Ha-Bin; Oh, In-Young; Shin, Inji; Kim, Won-Suk
- Ewha Authors
- SCOPUS Author ID
- Issue Date
- Journal Title
- ORGANIC LETTERS
- 1523-7060; 1523-7052
- vol. 19, no. 22, pp. 6224 - 6227
- AMER CHEMICAL SOC
- SCI; SCIE; SCOPUS
- 3-Hydroxy-2-(trialkylsilyl)phenyl triflates are presented as new versatile hydroxyaryne precursors. These are base-activated aryne precursors induced via a C-sp(2)-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.
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