scholarly journals Pd-CuFe Catalyst for Transfer Hydrogenation of Nitriles: Controllable Selectivity to Primary Amines and Secondary Amines

iScience ◽  
2018 ◽  
Vol 8 ◽  
pp. 61-73 ◽  
Author(s):  
Lei Liu ◽  
Yuhong Liu ◽  
Yongjian Ai ◽  
Jifan Li ◽  
Junjie Zhou ◽  
...  
Keyword(s):  
Transfer Hydrogenation ◽  
Secondary Amines ◽  
Primary Amines ◽  
Hydrogenation Of Nitriles

scholarly journals Tuning the selectivity of catalytic nitriles hydrogenation by structure regulation in atomically dispersed Pd catalysts

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Zhibo Liu ◽  
Fei Huang ◽  
Mi Peng ◽  
Yunlei Chen ◽  
Xiangbin Cai ◽  
...  
Keyword(s):  
Density Functional ◽  
Dissociative Adsorption ◽  
Transfer Hydrogenation ◽  
Secondary Amines ◽  
Primary Amines ◽  
Product Selectivity ◽  
Pd Catalysts ◽  
Catalytic Transfer ◽  
Pd Clusters ◽  
Hydrogenation Of Nitriles

AbstractThe product selectivity in catalytic hydrogenation of nitriles is strongly correlated with the structure of the catalyst. In this work, two types of atomically dispersed Pd species stabilized on the defect-rich nanodiamond-graphene (ND@G) hybrid support: single Pd atoms (Pd1/ND@G) and fully exposed Pd clusters with average three Pd atoms (Pdn/ND@G), were fabricated. The two catalysts show distinct difference in the catalytic transfer hydrogenation of nitriles. The Pd1/ND@G catalyst preferentially generates secondary amines (Turnover frequency (TOF@333 K 709 h−1, selectivity >98%), while the Pdn/ND@G catalyst exhibits high selectivity towards primary amines (TOF@313 K 543 h−1, selectivity >98%) under mild reaction conditions. Detailed characterizations and density functional theory (DFT) calculations show that the structure of atomically dispersed Pd catalysts governs the dissociative adsorption pattern of H2 and also the hydrogenation pathway of the benzylideneimine (BI) intermediate, resulting in different product selectivity over Pd1/ND@G and Pdn/ND@G, respectively. The structure-performance relationship established over atomically dispersed Pd catalysts provides valuable insights for designing catalysts with tunable selectivity.

Ruthenium-Catalyzed Transfer Hydrogenation of Nitriles: Reduction and SubsequentN-Monoalkylation to Secondary Amines

2013 ◽  
Vol 2013 (18) ◽  
pp. 3671-3674 ◽  
Author(s):  
Svenja Werkmeister ◽  
Christoph Bornschein ◽  
Kathrin Junge ◽  
Matthias Beller
Keyword(s):  
Transfer Hydrogenation ◽  
Secondary Amines ◽  
Hydrogenation Of Nitriles

Selective catalytic transfer hydrogenation of nitriles to primary amines using Pd/C

2014 ◽  
Vol 4 (3) ◽  
pp. 629 ◽  
Author(s):  
Marcelo Vilches-Herrera ◽  
Svenja Werkmeister ◽  
Kathrin Junge ◽  
Armin Börner ◽  
Matthias Beller
Keyword(s):  
Transfer Hydrogenation ◽  
Primary Amines ◽  
Catalytic Transfer Hydrogenation ◽  
Catalytic Transfer ◽  
Hydrogenation Of Nitriles

ChemInform Abstract: Ruthenium-Catalyzed Transfer Hydrogenation of Nitriles: Reduction and Subsequent N-Monoalkylation to Secondary Amines.

ChemInform ◽  
2013 ◽  
Vol 44 (45) ◽  
pp. no-no
Author(s):  
Svenja Werkmeister ◽  
Christoph Bornschein ◽  
Kathrin Junge ◽  
Matthias Beller
Keyword(s):  
Transfer Hydrogenation ◽  
Secondary Amines ◽  
Hydrogenation Of Nitriles

Chemoselective transfer hydrogenation of nitriles to secondary amines with nickel(II) catalysts

2021 ◽  
Vol 511 ◽  
pp. 111738
Author(s):  
Vincent Vermaak ◽  
Hermanus C.M. Vosloo ◽  
Andrew J. Swarts
Keyword(s):  
Transfer Hydrogenation ◽  
Secondary Amines ◽  
Hydrogenation Of Nitriles

A ppm level Rh-based composite as an ecofriendly catalyst for transfer hydrogenation of nitriles: triple guarantee of selectivity for primary amines

2019 ◽  
Vol 21 (6) ◽  
pp. 1390-1395 ◽  
Author(s):  
Lei Liu ◽  
Jifan Li ◽  
Yongjian Ai ◽  
Yuhong Liu ◽  
Jialiang Xiong ◽  
...  
Keyword(s):  
Transfer Hydrogenation ◽  
Primary Amines ◽  
Rh Catalyst ◽  
Ppm Level ◽  
Hydrogenation Of Nitriles

A 49 ppm Rh catalyst selectively transforms nitriles into primary amines with economical HCOOH and exhibits a TOF value of 6803 h−1.

Acceptorless amine dehydrogenation and transamination using Pd-doped layered double hydroxides

2018 ◽  
Author(s):  
Diana Ainembabazi ◽  
Nan An ◽  
Jinesh Manayil ◽  
Kare Wilson ◽  
Adam Lee ◽  
...  
Keyword(s):  
Layered Double Hydroxides ◽  
Oxidation States ◽  
Secondary Amines ◽  
Primary Amines ◽  
Acid Dissolution ◽  
Oxidative Amination ◽  
Strong Function ◽  
Excellent Activity ◽  
High Yields ◽  
Double Hydroxides

<div> <p>The synthesis, characterization, and activity of Pd-doped layered double hydroxides (Pd-LDHs) for for acceptorless amine dehydrogenation is reported. These multifunctional catalysts comprise Brønsted basic and Lewis acidic surface sites that stabilize Pd species in 0, 2+, and 4+ oxidation states. Pd speciation and corresponding cataytic performance is a strong function of metal loading. Excellent activity is observed for the oxidative transamination of primary amines and acceptorless dehydrogenation of secondary amines to secondary imines using a low Pd loading (0.5 mol%), without the need for oxidants. N-heterocycles, such as indoline, 1,2,3,4-tetrahydroquinoline, and piperidine, are dehydrogenated to the corresponding aromatics with high yields. The relative yields of secondary imines are proportional to the calculated free energy of reaction, while yields for oxidative amination correlate with the electrophilicity of primary imine intermediates. Reversible amine dehydrogenation and imine hydrogenation determine the relative imine:amine selectivity. Poisoning tests evidence that Pd-LDHs operate heterogeneously, with negligible metal leaching; catalysts can be regenerated by acid dissolution and re-precipitation.</p> </div> <br>

Cyclic amidines derived from benz[c,d]indole and 4,5-dihydro-3H-1-benzazepine including some related compounds: Synthesis and pharmacological screening

1985 ◽  
Vol 50 (8) ◽  
pp. 1888-1898 ◽  
Author(s):  
Miroslav Protiva ◽  
Zdeněk Šedivý ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jiří Němec
Keyword(s):  
Titanium Tetrachloride ◽  
Aqueous Sodium Hydroxide ◽  
Secondary Amines ◽  
Primary Amines ◽  
Open Chain ◽  
Lithium Aluminium ◽  
Pharmacological Screening ◽  
Antiinflammatory Effects ◽  
Related Compounds ◽  
Sodium Amide

Reactions of naphthostyril (I) with primary and secondary amines and titanium tetrachloride afforded cyclic amidines III-IX. Hydrogenation of I on Pd-C resulted in the 6,7,8,8a-tetrahydro derivative X which gave by treatment with sodium amide and 3-dimethylaminopropyl chloride the N-(aminoalkyl) compound XI. Reduction of I and its N-methyl derivative II with sodium amalgam in aqueous sodium hydroxide gave the 2a,3,4,5-tetrahydro derivatives XII and XIII. Reaction of XIII with sodium amide and 3-dimethylaminopropyl chloride afforded the 2a-(aminoalkyl) compound XIV. 1,3,4,5-Tetrahydro-1-benzazepin-2-one (XV) treated with primary amines and titanium tetrachloride gave the amidines XVI-XVIII. 3-Methyl-7,8,9,9a-tetrahydro-1H-benz[d,e]isoquinoline (XIX) was reduced with sodium borohydride to compound XX which was alkylated with propargyl bromide to 1-methyl-2-propargyl-2,3,3a,4,5,6-hexahydro-1H-benz[d,e]isoquinoline (XXI). An attempt to prepare the 2-(2-phenylethyl) analogue by treatment of compound XX with phenylacetyl chloride and by the following reduction with lithium aluminium hydride resulted in the open-chain amine XXII. The lactams I, II, X, and XIII showed some discoordinating, hypothermic, peripheral vasodilating, hyperglycaemic, diuretic and antiinflammatory effects. The amidines III-IX and XVI-XVIII had local anaesthetic, slight hypotensive, antiarrhythmic, peripheral myorelaxant, papaverine-like spasmolytic and thiopental potentiating effects.

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