(η5-Pentamethylcyclopentadienyl)iridium Complex Catalyzed Imine Reductions Utilizing the Biomimetic 1,4-NAD(P)H Cofactor andN-Benzyl-1,4-dihydronicotinamide as the Hydride-Transfer Agent
- Resource Type
- Authors
- Mathieu Soetens; Olivier Riant; Fleur Drouet
- Source
- ChemCatChem. 9:929-933
- Subject
- 010405 organic chemistry
Chemistry
Hydride
Bioorganometallic chemistry
Organic Chemistry
Imine
Cationic polymerization
Alkylation
010402 general chemistry
01 natural sciences
Combinatorial chemistry
Catalysis
0104 chemical sciences
Inorganic Chemistry
chemistry.chemical_compound
Transfer agent
Biomimetic synthesis
Organic chemistry
Physical and Theoretical Chemistry
- Language
- ISSN
- 1867-3880
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*=η5-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.