Strained-three membered rings are important synthons in modern organic chemistry. 1,10-Phenanthroline (phen) supported copper(II) systems have shown a long history of supporting cyclopropanation reactions by activating diazo carbonyl compounds for reactions with olefins. Here we report our efforts to characterize several phen derivatives, including 4,5-Diazafluoren-9-one (DAFO)–based ligand systems, to support copper(II)-dependent carbene transfer reaction to olefins and imines to form cyclopropane and aziridine rings, respectively. This includes several targeted ligand systems that can integrate into biomacromolecular chiral auxiliaries to support stereoselective transformations. Beyond the catalysis reported here, the copper(II) complexes will be characterized, and their structures were investigated through by 1H-NMR, 13C-NMR, FTIR, HPLC, UV-Vis, cyclic voltammetry (CV) and XRD analysis.

Copper(II)–catalyzed carbene transfer reactions: Toward stereoselective access to cyclopropanes and aziridines

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