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.

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.

scholarly journals Catalytic Transfer Hydrogenation and Acid Reactions of Furfural and 5-(Hydroxymethyl)Furfural over Hf-TUD-1 Type Catalysts

Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7203
Author(s):  
Margarida M. Antunes ◽  
Andreia F. Silva ◽  
Carolina D. Bernardino ◽  
Auguste Fernandes ◽  
Filipa Ribeiro ◽  
...  
Keyword(s):  
Kinetic Modelling ◽  
Transfer Hydrogenation ◽  
Catalytic Transfer Hydrogenation ◽  
Reaction Conditions ◽  
Renewable Chemicals ◽  
Hydroxymethyl Furfural ◽  
Platform Chemicals ◽  
Initial Substrate ◽  
Ordered Mesoporous ◽  
Catalytic Transfer

Heterogeneous catalysis, which has served well the petrochemical industry, may valuably contribute towards a bio-based economy by sustainably enabling selective reactions to renewable chemicals. Carbohydrate-containing matter may be obtained from various widespread sources and selectively converted to furanic platform chemicals: furfural (Fur) and 5-(hydroxymethyl)furfural (Hmf). Valuable bioproducts may be obtained from these aldehydes via catalytic transfer hydrogenation (CTH) using alcohols as H-donors under relatively moderate reaction conditions. Hafnium-containing TUD-1 type catalysts were the first of ordered mesoporous silicates explored for the conversion of Fur and Hmf via CTH/alcohol strategies. The materials promoted CTH and acid reactions leading to the furanic ethers. The bioproducts spectrum was broader for the reaction of Fur than of Hmf. A Fur reaction mechanism based on literature data was discussed and supported by kinetic modelling. The influence of the Hf loading and reaction conditions (catalyst load, type of alcohol H-donor, temperature, initial substrate concentration) on the reaction kinetics was studied. The reaction conditions were optimized to maximize the yields of 2-(alkoxymethyl)furan ethers formed from Fur; up to 63% yield was reached at 88% Fur conversion, 4 h/150 °C, using Hf-TUD-1(75), which was a stable catalyst. The Hf-TUD-1(x) catalysts promoted the selective conversion of Hmf to bis(2-alkoxymethyl)furan; e.g., 96% selectivity at 98% Hmf conversion, 3 h/170 °C for Hf-TUD-1(50).

scholarly journals Removal of benzylidene acetal and benzyl ether in carbohydrate derivatives using triethylsilane and Pd/C

2013 ◽  
Vol 9 ◽  
pp. 74-78 ◽  
Author(s):  
Abhishek Santra ◽  
Tamashree Ghosh ◽  
Anup Kumar Misra
Keyword(s):  
Room Temperature ◽  
Transfer Hydrogenation ◽  
Benzyl Ether ◽  
Catalytic Transfer Hydrogenation ◽  
Excellent Yield ◽  
Benzyl Ethers ◽  
Catalytic Transfer

Clean deprotection of carbohydrate derivatives containing benzylidene acetals and benzyl ethers was achieved under catalytic transfer hydrogenation conditions by using a combination of triethylsilane and 10% Pd/C in CH3OH at room temperature. A variety of carbohydrate diol derivatives were prepared from their benzylidene derivatives in excellent yield.

Ruthenium (ii) complexes with c- and c-symmetric bis-(+)-camphopyrazole ligands and their evaluation in catalytic transfer hydrogenation of aldehydes

2021 ◽  
pp. 120429
Author(s):  
Christian O. Blanco ◽  
Ligia Llovera ◽  
Alberto Herrera ◽  
Romano Dorta ◽  
Giuseppe Agrifoglio ◽  
...  
Keyword(s):  
Transfer Hydrogenation ◽  
Catalytic Transfer Hydrogenation ◽  
Catalytic Transfer

Influence of metal oxide and heteropoly tungustate location in mesoporous silica towards catalytic transfer hydrogenation of furfural to γ-valerolactone

2021 ◽  
Author(s):  
Bolla Srinivasarao ◽  
Yogita Y ◽  
Dhana Lakshmi Darsi ◽  
Krishna Kumari Pamula ◽  
N. Lingaiah
Keyword(s):  
Mesoporous Silica ◽  
Metal Oxide ◽  
Transfer Hydrogenation ◽  
Catalytic Transfer Hydrogenation ◽  
One Pot ◽  
Catalytic Transfer

One pot conversion of furfural to -valerolactone by transfer hydrogenation has been achieved over bifunctional Zr and TPA located in mesoporous silica catalysts. Different catalysts with TPA and ZrO2 located...

Synergistic Effect of B and N Dopants in Catalytic Transfer Hydrogenation

2018 ◽  
Vol 7 (6) ◽  
pp. 1107-1112 ◽  
Author(s):  
Yunrui Zhang ◽  
Yingying Zhai ◽  
Minzhe Chu ◽  
Li Huo ◽  
Haijun Wang ◽  
...  
Keyword(s):  
Synergistic Effect ◽  
Transfer Hydrogenation ◽  
Catalytic Transfer Hydrogenation ◽  
Catalytic Transfer

Transfer hydrogenation of biomass-derived levulinic acid to γ-valerolactone over supported Ni catalysts

RSC Advances ◽  
2016 ◽  
Vol 6 (64) ◽  
pp. 59753-59761 ◽  
Author(s):  
A. M. Hengne ◽  
B. S. Kadu ◽  
N. S. Biradar ◽  
R. C. Chikate ◽  
C. V. Rode
Keyword(s):  
Levulinic Acid ◽  
Transfer Hydrogenation ◽  
Complete Conversion ◽  
Catalytic Transfer Hydrogenation ◽  
Ni Catalysts ◽  
Catalytic Transfer ◽  
Supported Ni Catalysts ◽  
Supported Ni

A bifunctional Ni/MMT catalyst for catalytic transfer hydrogenation of levulinic acid to γ-valerolactone with complete conversion and selectivity.

Sign in / Sign up

Export Citation Format

Share Document