Switching Selectivity in Copper-Catalyzed Transfer Hydrogenation of Nitriles to Primary Amine-Boranes and Secondary Amines under Mild Conditions

2021 ◽  
Author(s):  
Hao Song ◽  
Yao Xiao ◽  
Zhuohua Zhang ◽  
Wanjin Xiong ◽  
Ren Wang ◽  
...  
Keyword(s):  
Primary Amine ◽  
Transfer Hydrogenation ◽  
Secondary Amines ◽  
Mild Conditions ◽  
Amine Boranes ◽  
Hydrogenation Of Nitriles

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

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

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.

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

Phosphine-Free Manganese Catalyst Enables Selective Transfer Hydrogenation of Nitriles to Primary and Secondary Amines Using Ammonia–Borane

ACS Catalysis ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 2786-2794
Author(s):  
Koushik Sarkar ◽  
Kuhali Das ◽  
Abhishek Kundu ◽  
Debashis Adhikari ◽  
Biplab Maji
Keyword(s):  
Ammonia Borane ◽  
Transfer Hydrogenation ◽  
Secondary Amines ◽  
Selective Transfer ◽  
Primary And Secondary Amines ◽  
Hydrogenation Of Nitriles

Metal-free nitrogen -doped carbon nanosheets: a catalyst for the direct synthesis of imines under mild conditions

2019 ◽  
Vol 21 (9) ◽  
pp. 2448-2461 ◽  
Author(s):  
Kaizhi Wang ◽  
Pengbo Jiang ◽  
Ming Yang ◽  
Ping Ma ◽  
Jiaheng Qin ◽  
...  
Keyword(s):  
Direct Synthesis ◽  
Catalytic Performance ◽  
Transfer Hydrogenation ◽  
Carbon Nanosheets ◽  
Nitrogen Doped ◽  
Metal Free ◽  
Mild Conditions ◽  
Nitrogen Doped Carbon ◽  
Hydrogenation Of Nitriles

Herein, a highly stable, porous, multifunctional and metal-free catalyst was developed, which exhibited significant catalytic performance in the oxidation of amines and the transfer hydrogenation of nitriles under mild conditions.

scholarly journals Quasi Pd1Ni single-atom surface alloy catalyst enables hydrogenation of nitriles to secondary amines

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Hengwei Wang ◽  
Qiquan Luo ◽  
Wei Liu ◽  
Yue Lin ◽  
Qiaoqiao Guan ◽  
...  
Keyword(s):  
Building Blocks ◽  
Surface Alloy ◽  
Secondary Amines ◽  
Single Atom ◽  
Redox Potentials ◽  
Practical Applications ◽  
Mild Conditions ◽  
Metal Selectivity ◽  
High Yields ◽  
Hydrogenation Of Nitriles

Abstract Hydrogenation of nitriles represents as an atom-economic route to synthesize amines, crucial building blocks in fine chemicals. However, high redox potentials of nitriles render this approach to produce a mixture of amines, imines and low-value hydrogenolysis byproducts in general. Here we show that quasi atomic-dispersion of Pd within the outermost layer of Ni nanoparticles to form a Pd1Ni single-atom surface alloy structure maximizes the Pd utilization and breaks the strong metal-selectivity relations in benzonitrile hydrogenation, by prompting the yield of dibenzylamine drastically from ∼5 to 97% under mild conditions (80 °C; 0.6 MPa), and boosting an activity to about eight and four times higher than Pd and Pt standard catalysts, respectively. More importantly, the undesired carcinogenic toluene by-product is completely prohibited, rendering its practical applications, especially in pharmaceutical industry. Such strategy can be extended to a broad scope of nitriles with high yields of secondary amines under mild conditions.

Selective synthesis of secondary amines from nitriles using Pt nanowires as a catalyst

2014 ◽  
Vol 50 (26) ◽  
pp. 3512-3515 ◽  
Author(s):  
Shuanglong Lu ◽  
Jiaqing Wang ◽  
Xueqin Cao ◽  
Xinming Li ◽  
Hongwei Gu
Keyword(s):  
Secondary Amines ◽  
Selective Synthesis ◽  
Mild Conditions ◽  
Hydrogenation Of Nitriles ◽  
Pt Nanowires

A series of both symmetrical and unsymmetrical secondary amines are synthesized from hydrogenation of nitriles under mild conditions.

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
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