Department of Chemistry and Nano Science, Ewha Womans University , Seoul 03760, Korea.
Department of Drug Discovery Research, Korea Research Institute of Chemical Technology , Daejeon 34602, Korea.
Org Lett. 2017 Nov 17;19(22):6224-6227. doi: 10.1021/acs.orglett.7b03160. Epub 2017 Nov 7.
3-Hydroxy-2-(trialkylsilyl)phenyl triflates are presented as new versatile hydroxyaryne precursors. These are base-activated aryne precursors induced via a C-sp-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.
3-羟基-2-(三烷基硅基)苯基三氟甲磺酸酯被提出作为新型多功能羟基芳炔前体。这些是通过 C-sp 到 O1,3-Brook 重排引发的碱激活芳炔前体。各种芳基亲电试剂与 3-羟基-2-(三烷基硅基)苯基三氟甲磺酸酯生成的 3-三烷基硅氧基苯炔反应，有效地得到了高区域选择性的苯酚衍生物。此外，通过交叉实验，证明了硅烷基迁移的分子内机制。
