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

• DOI: 10.1021/acs.orglett.7b03160
• Publication Date: 2017-11-07T17:04:44Z
• Authors: Yong-Ju Kwon; Young-Kyo Jeon; Ha-Bin Sim; In-Young Oh; Inji Shin; Won-Suk Kim
• Keywords: 01 natural sciences; 0104 chemical sciences

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.