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3-Hydroxy-2-(trialkylsilyl)phenyl Triflate: A Benzyne Precursor Triggered via 1,3-C-sp2-to-O Silyl Migration
Organic Letters ( IF 5.2 ) Pub Date : 2017-11-07 00:00:00 , DOI: 10.1021/acs.orglett.7b03160
Yong-Ju Kwon 1 , Young-Kyo Jeon 1 , Ha-Bin Sim 1 , In-Young Oh 1 , Inji Shin 2, 3 , Won-Suk Kim 1
Affiliation  

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.

中文翻译:

3-羟基-2-(三烷基甲硅烷基)苯基三氟甲磺酸酯:通过1,3-C-sp 2 -O甲硅烷基迁移引发的苯炔前体

3-羟基-2-(三烷基甲硅烷基)苯基三氟甲磺酸酯是新的通用羟基芳烃前体。它们是通过C-sp 2 -O-O 1,3-Brook重排诱导的碱活化的芳烃前体。由3-羟基-2-(三烷基甲硅烷基)苯基三氟甲磺酸酯产生的各种亲嗜碱和3-三烷基甲硅烷氧基苯并ben的反应有效地提供了高度区域选择性的苯酚衍生物。此外,通过交叉实验,证明了甲硅烷基迁移的分子内机理。
更新日期:2017-11-07
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