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

doi:10.1021/acs.orglett.7b03160

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

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

20 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 language	English
Pages (from-to)	6224-6227
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.7b03160
State	Published - 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.

Access to Document

10.1021/acs.orglett.7b03160

Cite this

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

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.",

author = "Kwon, {Yong Ju} and Jeon, {Young Kyo} and Sim, {Ha Bin} and Oh, {In Young} and Inji Shin and Kim, {Won Suk}",

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: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = nov,

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doi = "10.1021/acs.orglett.7b03160",

language = "English",

volume = "19",

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journal = "Organic Letters",

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TY - JOUR

T1 - 3-Hydroxy-2-(trialkylsilyl)phenyl Triflate

T2 - A Benzyne Precursor Triggered via 1,3-C-sp2-to-O Silyl Migration

AU - Kwon, Yong Ju

AU - Jeon, Young Kyo

AU - Sim, Ha Bin

AU - Oh, In Young

AU - Shin, Inji

AU - Kim, Won Suk

N1 - 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.

PY - 2017/11/17

Y1 - 2017/11/17

N2 - 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.

AB - 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.

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