Selective Synthesis of Symmetrical Secondary Amines from Nitriles with a Pt−CuFe/Fe<sub>3</sub>O<sub>4</sub> Catalyst and Ammonia Borane as Hydrogen Donor

Guo, Rong; He, Guannan; Liu, Lei; Ai, Yongjian; Hu, Zenan; Zhang, Xinyue; Tian, Haimeng; Sun, Hong; Niu, Dapeng; Liang, Qionglin

doi:10.1002/cplu.202000028

Cited by 8 publications

(3 citation statements)

References 51 publications

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“…In this study, several lines of evidence clearly suggested that exogenous application with AB, a solid and relatively idealized H 2 donor in industry [ 38 ], could attenuate cold stress-induced rapeseeds growth and photosynthetic inhibition in both laboratory and field levels. The evidence includes: (i) simultaneous treatment with AB in both laboratory and field experiments obviously recovered the inhibited seedling growth and decreased photosynthesis caused by cold stress (evaluated by the changes in chlorophyll content and Pn, Gs, and Ci; Figs.…”

Section: Discussionmentioning

confidence: 82%

“…Considering the future application in large scale agriculture, seeking a more convenient and safer H 2 supply in crop-plantation, forestry, and animal husbandry, was a challenge for scientific community [ 37 ]. Ammonia borane (NH 3 BH 3 ; AB) is a potential alternative hydrogen donor in field of chemical industry [ 38 ] because of its high hydrogen capacity (19.6%) [ 39 , 40 ]. In addition to H 2 , AB was hydrolyzed into trace amounts of ammonium ions and metaborate ions, both of which were beneficial for plant growth [ 41 , 42 ].…”

Section: Introductionmentioning

confidence: 99%

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Ammonia borane positively regulates cold tolerance in Brassica napus via hydrogen sulfide signaling

et al. 2022

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Background Cold stress adversely influences rapeseeds (Brassica napus L.) growth and yield during winter and spring seasons. Hydrogen (H2) is a potential gasotransmitter that is used to enhance tolerance against abiotic stress, including cold stress. However, convenience and stability are two crucial limiting factors upon the application of H2 in field agriculture. To explore the application of H2 in field, here we evaluated the role of ammonia borane (AB), a new candidate for a H2 donor produced by industrial chemical production, in plant cold tolerance. Results The application with AB could obviously alleviate the inhibition of rapeseed seedling growth and reduce the oxidative damage caused by cold stress. The above physiological process was closely related to the increased antioxidant enzyme system and reestablished redox homeostasis. Importantly, cold stress-triggered endogenous H2S biosynthesis was further stimulated by AB addition. The removal or inhibition of H2S synthesis significantly abolished plant tolerance against cold stress elicited by AB. Further field experiments demonstrated that the phenotypic and physiological performances of rapeseed plants after challenged with cold stress in the winter and early spring seasons were significantly improved by administration with AB. Particularly, the most studied cold-stress response pathway, the ICE1-CBF-COR transcriptional cascade, was significantly up-regulated either. Conclusion Overall, this study clearly observed the evidence that AB-increased tolerance against cold stress could be suitable for using in field agriculture by stimulation of H2S signaling.

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Section: Discussionmentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Ammonia borane positively regulates cold tolerance in Brassica napus via hydrogen sulfide signaling

et al. 2022

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“…It should be pointed out that amines containing multifluorinated aromatic rings are very important intermediates in pharmaceutical synthesis . Surprisingly, catalytic reduction of nitrile has rarely been explored to synthesize this type of amine intermediate. , The preparation of (2,4,6-trifluorophenyl)methanamine hydrochloride ( 17 ) and (2-bromo-4,5-difluorophenyl)methanamine hydrochloride ( 19 ) was documented in only some patents through multistep processes. Compounds 17 and 19 were successfully isolated in good yields through this catalyst-free protocol.…”

Section: Results and Discussionmentioning

confidence: 99%

Noncatalyzed Reduction of Nitriles to Primary Amines with Ammonia Borane

et al. 2022

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The preparation of primary amines from nitriles has been a subject of continuing interest, and many different methods have been reported for this process. We report in this paper an alternative method for transforming nitriles into primary amines. In this work, a wide range of nitriles were reduced to primary amines by 1.2 equiv of ammonia borane under thermal decomposition conditions without any catalyst and the corresponding primary amines were isolated in good to excellent yields. The reactions are environmentally benign with H 2 and NH 3 generated as byproducts. The reactions are also tolerant of many functional groups. Nitriles are likely reduced by the in situ-generated aminodiborane, the application of which in organic synthesis has never been reported before. By using our protocol, primary amines containing multifluorinated aromatic rings, which are greatly important in pharmaceutical synthesis and have rarely been prepared via catalytic processes, were successfully prepared.

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Ultrathin Modified Silica “Skin” for the Transfer Hydrogenation Catalyst: Improving Selectivity by Adjusting Surface Wettability

Guo

Chen

et al. 2021

Adv Materials Inter

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Surface wettability of heterogeneous catalysts plays a crucial role in the catalytic activity and selectivity. In this work, an ultra‐thin modified silica coating is firstly used as the “skin” to adjust the surface hydrophilicity of the catalyst, which promotes the catalytic activity and selectivity in the transfer hydrogenation of nitriles. The ultrathin‐modified silica “skin” with 2–3 nm thickness is fabricated by the consecutive hydrolysis of (3‐aminopropyl)triethoxysilane and n‐propyltriethoxysilane, and the bimetallic catalyst Fe3O4@PtCu is encapsulated in the coating. The modified catalyst demonstrated significant catalytic efficiency for hydrogenation of benzonitrile to dibenzylamine. The reaction performs 93% conversion and 99% selectivity in “green” solvent H2O. Furthermore, the modified silica “skin” encapsulates the PtCu nanoparticles to prevent the leaching of active sites, thus brings excellent catalytic recyclability. More than Fe3O4@PtCu, the modified silica “skin” is applicable to a diverse range of catalysts, that is, PtCu/SiO2, PtCu/Al2O3, and PtCu/UiO‐66, endowing them with additional catalytic activity and selectivity in the hydrogenation of nitriles.

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Selective Synthesis of Symmetrical Secondary Amines from Nitriles with a Pt−CuFe/Fe₃O₄ Catalyst and Ammonia Borane as Hydrogen Donor

Cited by 8 publications

References 51 publications

Ammonia borane positively regulates cold tolerance in Brassica napus via hydrogen sulfide signaling

Ammonia borane positively regulates cold tolerance in Brassica napus via hydrogen sulfide signaling

Noncatalyzed Reduction of Nitriles to Primary Amines with Ammonia Borane

Ultrathin Modified Silica “Skin” for the Transfer Hydrogenation Catalyst: Improving Selectivity by Adjusting Surface Wettability

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Selective Synthesis of Symmetrical Secondary Amines from Nitriles with a Pt−CuFe/Fe3O4 Catalyst and Ammonia Borane as Hydrogen Donor

Cited by 8 publications

References 51 publications

Ammonia borane positively regulates cold tolerance in Brassica napus via hydrogen sulfide signaling

Ammonia borane positively regulates cold tolerance in Brassica napus via hydrogen sulfide signaling

Noncatalyzed Reduction of Nitriles to Primary Amines with Ammonia Borane

Ultrathin Modified Silica “Skin” for the Transfer Hydrogenation Catalyst: Improving Selectivity by Adjusting Surface Wettability

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Product

Resources

About

Selective Synthesis of Symmetrical Secondary Amines from Nitriles with a Pt−CuFe/Fe₃O₄ Catalyst and Ammonia Borane as Hydrogen Donor