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

Title
3-Hydroxy-2-(trialkylsilyl)phenyl Triflate: A Benzyne Precursor Triggered via 1,3-C-sp(2)-to-O Silyl Migration
Authors
Kwon, Yong-JuJeon, Young-KyoSim, Ha-BinOh, In-YoungShin, InjiKim, Won-Suk
Ewha Authors
김원석
SCOPUS Author ID
김원석scopus
Issue Date
2017
Journal Title
ORGANIC LETTERS
ISSN
1523-7060JCR Link1523-7052JCR Link
Citation
vol. 19, no. 22, pp. 6224 - 6227
Publisher
AMER CHEMICAL SOC
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
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.
DOI
10.1021/acs.orglett.7b03160
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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