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(η 5 ‐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
Author(s) -
Soetens Mathieu,
Drouet Fleur,
Riant Olivier
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201601307
Subject(s) - chemistry , hydride , imine , catalysis , transfer hydrogenation , iridium , cationic polymerization , cofactor , combinatorial chemistry , alkylation , amine gas treating , organometallic chemistry , redox , medicinal chemistry , photochemistry , organic chemistry , metal , ruthenium , enzyme
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.