Metal−Ligand Bifunctional Catalysis:  A Nonclassical Mechanism for Asymmetric Hydrogen Transfer between Alcohols and Carbonyl Compounds

2001 ◽  
Vol 66 (24) ◽  
pp. 7931-7944 ◽  
Author(s):  
Ryoji Noyori ◽  
Masashi Yamakawa ◽  
Shohei Hashiguchi
Keyword(s):  
Carbonyl Compounds ◽  
Hydrogen Transfer ◽  
Bifunctional Catalysis ◽  
Metal Ligand

Transfer Hydrogenation of Carbonyl Compounds and Alkenes Catalyzed by Ruthenium(II)-N-Heterocycle Carbene Complexes

2007 ◽  
Vol 72 (8) ◽  
pp. 1037-1045 ◽  
Author(s):  
Marianna Fekete ◽  
Ferenc Joó
Keyword(s):  
Carbonyl Compounds ◽  
Hydrogen Transfer ◽  
Transfer Hydrogenation ◽  
Unsaturated Alcohol ◽  
Two Phase ◽  
Carbene Complexes ◽  
Saturated Alcohol ◽  
Catalytic Activities ◽  
Saturated Aldehyde ◽  
Phase Mixture

The Ru(II)-N-heterocycle carbene complexes [RuCl2(η6-p-cymene)L] (L = 1-butyl-3-methylimid- azol-2-ylidene) and [RuCl(η6-p-cymene)L(pta)]Cl (pta = 1,3,5-triaza-7-phosphaadamantane) showed excellent catalytic activities (with turnover frequencies up to 1116 h-1) in the hydrogen transfer reduction of cinnamaldehyde and several ketones using propan-2-ol/KOH as a H-donor. Similar hydrogenations of trans-stilbene and cyclohexene were characterized by low conversions. The hydrogenation of 4-phenylbut-3-en-2-one and cinnamaldehyde proceeded with moderate selectivities of the formation of the saturated alcohol or of the of C=C hydrogenation (giving saturated ketone or saturated aldehyde). In the case of cinnamaldehyde, the unsaturated alcohol is initially formed; however, subsequent redox isomerization to the saturated aldehyde with the same catalyst diminishes its yield. The hydrogen transfer from formate to 4-phenylbut-3-en-2-one in an aqueous-organic two-phase mixture was also demonstrated.

ChemInform Abstract: Asymmetric Hydrogenation Through Metal-Ligand Bifunctional Catalysis

ChemInform ◽  
2008 ◽  
Vol 39 (3) ◽  
Author(s):  
Ryoji Noyori ◽  
Takeshi Ohkuma ◽  
Christian A. Sandoval ◽  
Kilian Muniz
Keyword(s):  
Asymmetric Hydrogenation ◽  
Bifunctional Catalysis ◽  
Metal Ligand

Hydrogen transfer reactions. I. Reduction of carbonyl compounds by alcohols catalyzed by alumina

1969 ◽  
Vol 47 (19) ◽  
pp. 3705-3707 ◽  
Author(s):  
D. V. Ramana ◽  
C. N. Pillai
Keyword(s):  
Vapor Phase ◽  
Carbonyl Compounds ◽  
Hydrogen Transfer ◽  
Isopropyl Alcohol ◽  
Aromatic Aldehydes ◽  
Transfer Reactions ◽  
Secondary Alcohols ◽  
Effective Catalyst ◽  
Phase Reduction ◽  
Aldehydes And Ketones

Alumina containing about 2.2% by weight of Na+ has been found to be an effective catalyst for the vapor phase reduction of carbonyl compounds by alcohols and for the reverse reaction, the oxidation of the alcohols by carbonyl compounds. The reduction of a number of aliphatic and aromatic aldehydes and ketones by isopropyl alcohol and the oxidation of a number of primary and secondary alcohols by ketones like acetone and cyclohexanone are reported.

Hydrogen-transfer reduction of α,β-unsaturated carbonyl compounds catalyzed by naphthyridine-functionalized N-heterocyclic carbene complexes

2016 ◽  
Vol 31 (8) ◽  
pp. e3673 ◽  
Author(s):  
Hsiao-Ching Huang ◽  
Mani Ramanathan ◽  
Yi-Hong Liu ◽  
Shie-Ming Peng ◽  
Shiuh-Tzung Liu
Keyword(s):  
Carbonyl Compounds ◽  
Hydrogen Transfer ◽  
Carbene Complexes
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