2020/04/23 by Kota Koshino, Rei Kinjo · 1 citation
Chemistry · #N-Heterocyclic Carbenes in Organic and Inorganic Chemistry #Organoboron and organosilicon chemistry #Synthesis and characterization of novel inorganic/organometallic compounds
paper · doi:10.1021/jacs.0c03179
openalex publication_date 2020/04/23 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01
Since the groundbreaking discovery in 2018 that the synthesis of a bottleable nucleophilic aluminyl anion is feasible, a handful of derivatives have been developed to date, which are, however, limited to diamino- and dialkyl-substituted species. Herein, we report the synthesis of a cyclic (alkyl)(amino)aluminyl anion based on a five-membered framework. The dicoordinate aluminum center features both a lone pair of electrons and an unoccupied 3p orbital, thus genuinely making it isoelectronic with carbenes. We show the bond formation and bond activation at the Al sphere: thus, not only does it undergo electron redistribution with borane to furnish a heteroatomic group 13 ring exhibiting a σ-aromatic nature concomitant with a three-center two-electron AlB 2 bond but also the ambiphilic nature allows for oxidative addition of Si–H, N–H, and even C–C bonds at the aluminum center.