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Updated: Apr 28, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
An anionic aluminabenzene bearing aromatic and ambiphilic contributions
Taichi Nakamura1, Katsunori Suzuki, Makoto Yamashita
1Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University , 1-13-27 Kasuga, Bunkyo-ku, 112-8551 Tokyo, Japan.
Abstract:
The synthesis and structure of an anionic aluminabenzene, which is the first example of an aluminum-containing heterobenzene, are reported. The molecular structure of this aluminabenzene exhibits a planar six-membered ring, and the absence of any bond alternation between its unsaturated bonds is consistent with the structural criteria of aromaticity. Theoretical calculations and the NMR spectroscopic analysis of this anionic aluminabenzene furthermore suggest that, in addition to the aromatic conjugation of six π-electrons, an ambiphilic contribution from a Lewis acidic aluminum center and an anionic pentadienyl moiety are present. Due to this contribution, the aluminabenzene is able to react with Lewis bases such as 4-dimethylaminopyridine and electrophiles such as methyl iodide.
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