(η5‐Pentamethylcyclopentadienyl)iridium Complex Catalyzed Imine Reductions Utilizing the Biomimetic 1, 4‐NAD(P)H Cofactor and N‐Benzyl‐1, 4‐dihydronicotinamide as the Hydride‐Transfer Agent. Issue 6 (8th February 2017)

• Record Type: Journal Article
• Authors: Soetens, Mathieu; Drouet, Fleur; Riant, Olivier
• Is Part Of: ChemCatChem. Volume 9:Issue 6(2017)
• Page Start: 929
• Page End: 933
• Publication Date: 2017-02-08
• Subjects: biomimetic synthesis -- bioorthogonal chemistry -- hydride transfer -- iridium -- reductive alkylation; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201601307
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: The interaction between synthetic organometallic complexes and metabolic cofactors has proven to be a newly emerging topic in bioorganometallic chemistry. Thus, the first cationic Cp*Ir‐catalyzed (Cp*=η 5 ‐pentamethylcyclopentadienyl) imine reduction in neutral buffered aqueous medium was examined. The reaction was found to proceed through hydride transfer from NADH as the hydride source at room temperature in air. Cationic Cp*Ir complexes proved to be the most efficient catalysts for this transformation. We also highlighted that the choice of the proton source was essential. The method was subsequently applied to cyclic and noncyclic imines. Eventually, the concept was extended to the reductive alkylation of one amine. Abstract : Transferring through : The first cationic Cp*Ir‐catalyzed imine reduction in neutral buffered aqueous medium in air at room temperature is reported. The reaction proceeds through hydride transfer from NADH as the hydride source. Cp*Ir(N, N) complexes are the most efficient catalysts for this transformation. The method is also applied to the reduction of cyclic and noncyclic imines and eventually extended to the reductive alkylation of an amine.