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

21 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

@article{bbd18de33ec948b1b73bba7c5253ecf3,

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,

day = "17",

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

language = "English",

volume = "19",

pages = "6224--6227",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "22",

}

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.

UR - https://www.scopus.com/pages/publications/85034566030

U2 - 10.1021/acs.orglett.7b03160

DO - 10.1021/acs.orglett.7b03160

M3 - Article

C2 - 29112429

AN - SCOPUS:85034566030

SN - 1523-7060

VL - 19

SP - 6224

EP - 6227

JO - Organic Letters

JF - Organic Letters

IS - 22