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Nucleophilic Diboration Strategy Targeting Diversified 1‐Boraphenarene Architectures
Author(s) -
Hirano Keiichi,
Morimoto Kensuke,
Fujioka Shota,
Miyamoto Kazunori,
Muranaka Atsuya,
Uchiyama Masanobu
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202009242
Subject(s) - chemoselectivity , chemistry , carbanion , boron , nucleophile , reagent , combinatorial chemistry , electrophile , nucleophilic addition , photochemistry , organic chemistry , catalysis
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 sp 2 ‐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 gives pseudo ‐enantio‐enriched boraphenarene, which emits circularly polarized fluorescence (CPL).