Nucleophilic Diboration Strategy Targeting Diversified 1‐Boraphenarene Architectures
Nucleophilic Diboration Strategy Targeting Diversified 1‐Boraphenarene Architectures
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针对多样化 1-Boraphenarene 结构的亲核硼化策略
DOI：
10.1002/anie.202009242
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Uchiyama Masanobu
中科院分区：
文献类型：
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作者：
Hirano Keiichi;Morimoto Kensuke;Fujioka Shota;Miyamoto Kazunori;Muranaka Atsuya;Uchiyama Masanobu
通过炔的亲核二硼化反应合成了一类硼掺杂的多环芳烃1-硼非那烯。用高碱性sp2-碳负离子活化二硼试剂，导致非常快速的连续C−B键形成，以构建硼杂环戊二烯。这种方法的特点是高化学选择性，提供了各种各样的1-boraphenarenes不同极性取代基。内环硼可方便地一锅芳基化，而外围硼可用于各种化学转化。高度非对映选择性的二硼化反应产生假对映体富集的硼苯芳烃，其发射圆偏振荧光（CPL）。
1‐Boraphenalenes, a class of boron‐doped polyaromatic hydrocarbons, were synthesized by nucleophilic diboration reaction of alkynes. Activation of diboron reagents with a highly basic sp2‐carbanion results in very fast successive C−B bond formations to construct the boracycle. This methodology is characterized by high chemoselectivity, affording a wide variety of 1‐boraphenarenes with diverse polar substituents. The endocyclic boron can be arylated conveniently in one pot, and the peripheral boron is available for various chemical transformations. Highly diastereoselective diboration givespseudo‐enantio‐enriched boraphenarene, which emits circularly polarized fluorescence (CPL).