Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 19, Pages 9057-9062Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c03179
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- Nanyang Technological University (NTU)
- Singapore Ministry of Education [MOE2018-T2-2-048(S)]
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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 sigma-aromatic nature concomitant with a three-center two-electron AlB2 bond but also the ambiphilic nature allows for oxidative addition of Si-H, N-H, and even C-C bonds at the aluminum center.
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