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Transfer Hydrogenation and Hydrogenation of Commercial‐Grade Aldehydes to Primary Alcohols Catalyzed by 2‐(Aminomethyl)pyridine and Pincer Benzo[ h ]quinoline Ruthenium Complexes
Author(s) -
Baldino Salvatore,
Facchetti Sarah,
ZanottiGerosa Antonio,
Nedden Hans Günter,
Baratta Walter
Publication year - 2016
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.201600420
Subject(s) - transfer hydrogenation , chemistry , pincer movement , quinoline , catalysis , medicinal chemistry , pyridine , ruthenium , butane , aldehyde , substrate (aquarium) , organic chemistry , alcohol , noyori asymmetric hydrogenation , diphenylphosphine oxide , oceanography , geology
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.