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

Yong Ju Kwon, Young Kyo Jeon, Ha Bin Sim, In Young Oh, Inji Shin, Won Suk Kim

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)6224-6227
Number of pages4
JournalOrganic Letters
Volume19
Issue number22
DOIs
StatePublished - 17 Nov 2017

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) (NRF-2015R1A1A1A05001334) and the New & Renewable Energy of the Korea Institute of Energy Technology Evaluation and Planning (KETEP) grant (No. 20163030013900).

Publisher Copyright:
© 2017 American Chemical Society.

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