Issue 9, 2024

Naphthyridine–2NO, a new C2-symmetric rigid tetradentate bimetallic ligand and its application in asymmetric Friedel–Crafts alkylation

Abstract

The development of dinuclear metal complexes as catalysts in asymmetric catalysis is in great demand but remains a particularly challenging goal. Herein, we rationally designed and developed a series of novel and easily accessed tertiary amine-derived C2-symmetric rigid tetradentate bimetallic naphthyridine-N,N′-dioxide ligands, namely Nar–2NO ligands, which incorporate the advantages of both the naphthyridine skeleton and the pyrroloimidazolone-based N-oxide moiety. The chiral dinuclear Nar–2NO–2Ni(II) complex is generated in situ avoiding isolation and handling of sensitive species, and it performed successfully in enantioselective Michael-type Friedel–Crafts alkylation reactions of indoles and β-nitrostyrenes, affording the chiral functionalized indole derivatives with up to 92% yield and 99% ee under mild conditions. These results demonstrated the promising utility of the tetradentate bimetallic naphthyridine–2NO ligands, which can coordinate two metals in close proximity to each other, in asymmetric catalysis.

Graphical abstract: Naphthyridine–2NO, a new C2-symmetric rigid tetradentate bimetallic ligand and its application in asymmetric Friedel–Crafts alkylation

Supplementary files

Article information

Article type
Research Article
Submitted
05 Feb 2024
Accepted
09 Mar 2024
First published
11 Mar 2024

Org. Chem. Front., 2024,11, 2600-2606

Naphthyridine–2NO, a new C2-symmetric rigid tetradentate bimetallic ligand and its application in asymmetric Friedel–Crafts alkylation

P. Hu, K. Xu, X. Wang, Z. Chen, W. Zhang, Y. Zhou, W. Zhang and X. Liu, Org. Chem. Front., 2024, 11, 2600 DOI: 10.1039/D4QO00248B

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