pH-Dependent Transfer Hydrogenation of Water-Soluble Carbonyl Compounds with [Cp*IrIII(H2O)3]2+(Cp* =η5-C5Me5) as a Catalyst Precursor and HCOONa as a Hydrogen Donor in Water

1999 ◽  
Vol 18 (26) ◽  
pp. 5470-5474 ◽  
Author(s):  
Seiji Ogo ◽  
Nobuyuki Makihara ◽  
Yoshihito Watanabe
Keyword(s):  
Carbonyl Compounds ◽  
Water Soluble ◽  
Hydrogen Donor ◽  
Transfer Hydrogenation ◽  
Catalyst Precursor ◽  
Ph Dependent

scholarly journals Iridium-Catalyzed Transfer Hydrogenation of Ketones and Aldehydes Using Glucose as a Sustainable Hydrogen Donor

Catalysts ◽  
2019 ◽  
Vol 9 (6) ◽  
pp. 503 ◽  
Author(s):  
Masato Yoshida ◽  
Ryota Hirahata ◽  
Takayoshi Inoue ◽  
Takuya Shimbayashi ◽  
Ken-ichi Fujita
Keyword(s):  
Catalytic System ◽  
Carbonyl Compounds ◽  
Hydrogen Donor ◽  
Transfer Hydrogenation ◽  
Environmentally Benign ◽  
Iridium Catalyst ◽  
Hydrogenation Reactions

A new catalytic system for transfer hydrogenation of carbonyl compounds using glucose as a hydrogen donor was developed. Various ketones and aldehydes were efficiently converted to corresponding alcohols with two equivalents of glucose in the presence of a small amount (0.1 to 1.0 mol%) of iridium catalyst that had a functional ligand. In this catalytic system, transfer hydrogenation reactions proceeded based on the cooperativity of iridium and a functional ligand. It should be noted that environmentally benign water could have been used as a solvent in the present catalytic system for the reduction of various carbonyl substrates. Furthermore, the reaction scope could be extended by using N,N-dimethylacetamide as a reaction solvent.

Highly selective transfer hydrogenation of α,β-unsaturated carbonyl compounds using Cu-based nanocatalysts

2017 ◽  
Vol 7 (13) ◽  
pp. 2828-2837 ◽  
Author(s):  
Nazia Siddqui ◽  
Bipul Sarkar ◽  
Chandrashekar Pendem ◽  
Rubina khatun ◽  
L. N. Sivakumar Konthala ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Hydrogen Donor ◽  
Transfer Hydrogenation ◽  
Selective Transfer ◽  
Unsaturated Alcohols

Simultaneous dehydrogenation of cyclohexanol to cyclohexanone and hydrogenation of α,β-unsaturated carbonyl compounds to corresponding α,β-unsaturated alcohols was carried out in a single pot reaction without addition of any external hydrogen donor.

pH-Dependent Transfer Hydrogenation of Ketones with HCOONa as a Hydrogen Donor Promoted by (η6-C6Me6)Ru Complexes

2002 ◽  
Vol 21 (14) ◽  
pp. 2964-2969 ◽  
Author(s):  
Seiji Ogo ◽  
Tsutomu Abura ◽  
Yoshihito Watanabe
Keyword(s):  
Hydrogen Donor ◽  
Transfer Hydrogenation ◽  
Ru Complexes ◽  
Ph Dependent

scholarly journals New Bifunctional Bis(azairidacycle) with Axial Chirality via Double Cyclometalation of 2,2′-Bis(aminomethyl)-1,1′-binaphthyl

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1165
Author(s):  
Yasuhiro Sato ◽  
Yuichi Kawata ◽  
Shungo Yasui ◽  
Yoshihito Kayaki ◽  
Takao Ikariya
Keyword(s):  
Hydrogen Transfer ◽  
Bond Cleavage ◽  
Enantiomeric Excess ◽  
Transfer Hydrogenation ◽  
Catalyst Precursor ◽  
Asymmetric Catalysts ◽  
Axially Chiral ◽  
Diastereomeric Mixture ◽  
Raney Ni ◽  
Half Sandwich

As a candidate for bifunctional asymmetric catalysts containing a half-sandwich C–N chelating Ir(III) framework (azairidacycle), a dinuclear Ir complex with an axially chiral linkage is newly designed. An expedient synthesis of chiral 2,2′-bis(aminomethyl)-1,1′-binaphthyl (1) from 1,1-bi-2-naphthol (BINOL) was accomplished by a three-step process involving nickel-catalyzed cyanation and subsequent reduction with Raney-Ni and KBH4. The reaction of (S)-1 with an equimolar amount of [IrCl2Cp*]2 (Cp* = η5–C5(CH3)5) in the presence of sodium acetate in acetonitrile at 80 °C gave a diastereomeric mixture of new dinuclear dichloridodiiridium complexes (5) through the double C–H bond cleavage, as confirmed by 1H NMR spectroscopy. A loss of the central chirality on the Ir centers of 5 was demonstrated by treatment with KOC(CH3)3 to generate the corresponding 16e amidoiridium complex 6. The following hydrogen transfer from 2-propanol to 6 provided diastereomers of hydrido(amine)iridium retaining the bis(azairidacycle) architecture. The dinuclear chlorido(amine)iridium 5 can serve as a catalyst precursor for the asymmetric transfer hydrogenation of acetophenone with a substrate to a catalyst ratio of 200 in the presence of KOC(CH3)3 in 2-propanol, leading to (S)-1-phenylethanol with up to an enantiomeric excess (ee) of 67%.

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