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

Org Lett. 2017 Nov 17;19(22):6224-6227. doi: 10.1021/acs.orglett.7b03160. Epub 2017 Nov 7.

Authors

Yong-Ju Kwon¹, Young-Kyo Jeon¹, Ha-Bin Sim¹, In-Young Oh¹, Inji Shin^{2

3}, Won-Suk Kim¹

Affiliations

¹ Department of Chemistry and Nano Science, Ewha Womans University , Seoul 03760, Korea.
² Department of Drug Discovery Research, Korea Research Institute of Chemical Technology , Daejeon 34602, Korea.
³ Department of Medicinal and Pharmaceutical Chemistry, University of Science and Technology , Daejeon 34101, Korea.

PMID: 29112429
DOI: 10.1021/acs.orglett.7b03160

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.

Publication types

Research Support, Non-U.S. Gov't