Journal
ORGANIC LETTERS
Volume 19, Issue 22, Pages 6224-6227Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03160
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Funding
- National Research Foundation of Korea (NRF) [NRF-2015R1A1A1A05001334]
- New & Renewable Energy of the Korea Institute of Energy Technology Evaluation and Planning (KETEP) [20163030013900]
- Korea Evaluation Institute of Industrial Technology (KEIT) [20163030013900] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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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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