Transfer Hydrogenation and Hydrogenation of Commercial‐Grade Aldehydes to Primary Alcohols Catalyzed by 2‐(Aminomethyl)pyridine and Pincer Benzo[<i>h</i>]quinoline Ruthenium Complexes

Abstract

Abstract The chemoselective reduction of commercial‐grade aldehydes (97–99 %) to primary alcohols is achieved with cis ‐[RuCl 2 (ampy)(PP)] [ampy=2‐(aminomethyl)pyridine; PP=1,4‐bis(diphenylphosphino)butane, 1,1′‐ferrocenediyl‐bis(diphenylphosphine)] and pincer [RuCl(CNN R )(PP)] [PP=1,3‐bis(diphenylphosphino)propane, 1,4‐bis(diphenylphosphino)butane, 1,1′‐ferrocenediyl‐bis(diphenylphosphine); HCNN R =4‐substituted‐2‐aminomethyl‐benzo[ h ]quinoline; R=Me, Ph] complexes by transfer hydrogenation and hydrogenation reactions. Aromatic, conjugated, and aliphatic aldehydes are converted quantitatively to the corresponding alcohols using 2‐propanol with potassium carbonate at substrate/catalyst ratios up to 100 000 by transfer hydrogenation, whereas aldehyde hydrogenation (5–20 atm of H 2 ) is achieved efficiently in MeOH in the presence of KO t Bu at substrate/catalyst ratios up to 40 000.