Palladium-catalyzed simple and efficient hydrogenative cleavage of azo compounds using recyclable polymer-supported formate

2005 ◽  
Vol 83 (5) ◽  
pp. 517-520 ◽  
Author(s):  
Keelara Abiraj ◽  
Gejjalagere R Srinivasa ◽  
D Channe Gowda
Keyword(s):  
Functional Groups ◽  
Room Temperature ◽  
Hydrogen Donor ◽  
Transfer Hydrogenation ◽  
Azo Compounds ◽  
Catalytic Transfer Hydrogenation ◽  
Palladium Catalyzed ◽  
Catalytic Transfer ◽  
Polymer Supported

Palladium-catalyzed room temperature transfer hydrogenation of azo compounds using recyclable polymer-supported formate as the hydrogen donor produces corresponding amine(s) in excellent yields (88%–98%). This method was found to be highly facile with selectivity over a number of other functional groups such as halogen, alkene, nitrile, carbonyl, amide, methoxy, and hydroxyl.Key words: azo compounds, catalytic transfer hydrogenation, polymer-supported formate, 10% Pd-C, amines.

Reductive Cleavage of Azo Compounds Catalysed by Commercial Zinc Dust and Hydrazinium Monoformate as a New Hydrogen Donor for Heterogeneous Catalytic Transfer Hydrogenation

2002 ◽  
Vol 2002 (8) ◽  
pp. 384-385 ◽  
Author(s):  
Shankare Gowda ◽  
K. Abiraj ◽  
D. Channe Gowda
Keyword(s):  
Zinc Dust ◽  
Reductive Cleavage ◽  
Hydrogen Donor ◽  
Transfer Hydrogenation ◽  
Azo Compounds ◽  
Catalytic Transfer Hydrogenation ◽  
Heterogeneous Catalytic ◽  
Catalytic Transfer ◽  
Reflux Temperature

Azo compounds are reductively cleaved to amine/s at reflux temperature within 15 min by employing less expensive commercial zinc dust and hydrazinium monoformate, a new hydrogen donor for catalytic transfer hydrogenation.

Polymer-Supported Formate and Magnesium: An Efficient Transfer Hydrogenation System for the Facile Reduction of Azo Compounds

2005 ◽  
Vol 2005 (2) ◽  
pp. 123-125 ◽  
Author(s):  
G. R. Srinivasa ◽  
K. Abiraj ◽  
D. Channe Gowda
Keyword(s):  
Efficient Method ◽  
Room Temperature ◽  
Low Cost ◽  
Selective Reduction ◽  
Hydrogen Donor ◽  
Transfer Hydrogenation ◽  
Azo Compounds ◽  
Magnesium Powder ◽  
Polymer Supported ◽  
Efficient Transfer

A mild and efficient method was developed for the chemo-selective reduction of azo compounds to the corresponding amine/s using recyclable polymer-supported formate as hydrogen donor in the presence of low cost magnesium powder at room temperature.

scholarly journals Reduction of the Diazo Functionality of α-Diazocarbonyl Compounds into a Methylene Group by NH3BH3 or NaBH4 Catalyzed by Au Nanoparticles

Nanomaterials ◽  
2021 ◽  
Vol 11 (1) ◽  
pp. 248
Author(s):  
Marios Kidonakis ◽  
Manolis Stratakis
Keyword(s):  
Room Temperature ◽  
Au Nanoparticles ◽  
Transfer Hydrogenation ◽  
Protic Solvent ◽  
Boron Hydride ◽  
Catalytic Transfer Hydrogenation ◽  
Reaction Conditions ◽  
Catalytic Transfer ◽  
Methylene Group

Supported Au nanoparticles on TiO2 (1 mol%) are capable of catalyzing the reduction of the carbene-like diazo functionality of α-diazocarbonyl compounds into a methylene group [C=(N2) → CH2] by NH3BH3 or NaBH4 in methanol as solvent. The Au-catalyzed reduction that occurs within a few minutes at room temperature formally requires one hydride equivalent (B-H) and one proton that originates from the protic solvent. This pathway is in contrast to the Pt/CeO2-catalyzed reaction of α-diazocarbonyl compounds with NH3BH3 in methanol, which leads to the corresponding hydrazones instead. Under our stoichiometric Au-catalyzed reaction conditions, the ketone-type carbonyls remain intact, which is in contrast to the uncatalyzed conditions where they are selectively reduced by the boron hydride reagent. It is proposed that the transformation occurs via the formation of chemisorbed carbenes on Au nanoparticles, having proximally activated the boron hydride reagent. This protocol is the first general example of catalytic transfer hydrogenation of the carbene-like α -ketodiazo functionality.

Catalytic transfer hydrogenation of azobenzene by low-valent nickel complexes: a route to 1,2-disubstituted benzimidazoles and 2,4,5-trisubstituted imidazolines

2016 ◽  
Vol 45 (25) ◽  
pp. 10389-10401 ◽  
Author(s):  
Daniel A. Zurita ◽  
Marcos Flores-Alamo ◽  
Juventino J. García
Keyword(s):  
Nickel Complexes ◽  
Hydrogen Donor ◽  
Transfer Hydrogenation ◽  
Catalytic Transfer Hydrogenation ◽  
One Pot ◽  
One Pot Synthesis ◽  
Catalytic Transfer ◽  
Low Valent ◽  
The One

The one-pot synthesis of 1,2-disubstituted benzimidazoles by the transfer hydrogenation of azobenzene, using benzylamine as a hydrogen donor is reported, catalyzed by 2 mol% of [Ni(COD)2] : dippe.

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