Ligand-Free (Z)-Selective Transfer Semihydrogenation of Alkynes Catalyzed by in situ Generated Oxidizable Copper Nanoparticles

10.26434/chemrxiv.13635272 ◽

2021 ◽

Author(s):

Rafał Kusy ◽

Karol Grela

Keyword(s):

Suzuki Reaction ◽

Ammonia Borane ◽

Water Soluble ◽

Selective Transfer ◽

One Pot ◽

Ammonia Complex ◽

Ligand Free ◽

Simple Phase ◽

Operational Simplicity

Herein, we present (Z)-selective transfer semihydrogenation of alkynes based on in situ generated CuNPs in the presence of hydrogen donors, such as ammonia-borane and a protic solvent. This environmentally-friendly method is characterized by operational simplicity combined with high stereo- and chemoselectivity and functional group compatibility. Auto-oxidation of CuNPs after the semihydrogenation reaction is completed results in the formation of water-soluble ammonia complex, so that the catalyst may be reused several times by simple phase-separation with no need of any special regeneration process. Formed NH4B(OR)4 can be easily transformed back to ammonia-borane or to boric acid. In addition, one-pot tandem sequence involving Suzuki reaction followed by semihydrogenation was presented.

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Ligand-Free (Z)-Selective Transfer Semihydrogenation of Alkynes Catalyzed by in situ Generated Oxidizable Copper Nanoparticles

10.26434/chemrxiv.13635272.v1 ◽

2021 ◽

Author(s):

Rafał Kusy ◽

Karol Grela

Keyword(s):

Suzuki Reaction ◽

Ammonia Borane ◽

Water Soluble ◽

Selective Transfer ◽

One Pot ◽

Ammonia Complex ◽

Ligand Free ◽

Simple Phase ◽

Operational Simplicity

Herein, we present (Z)-selective transfer semihydrogenation of alkynes based on in situ generated CuNPs in the presence of hydrogen donors, such as ammonia-borane and a protic solvent. This environmentally-friendly method is characterized by operational simplicity combined with high stereo- and chemoselectivity and functional group compatibility. Auto-oxidation of CuNPs after the semihydrogenation reaction is completed results in the formation of water-soluble ammonia complex, so that the catalyst may be reused several times by simple phase-separation with no need of any special regeneration process. Formed NH4B(OR)4 can be easily transformed back to ammonia-borane or to boric acid. In addition, one-pot tandem sequence involving Suzuki reaction followed by semihydrogenation was presented.

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Facile in situ synthesis of copper nanoparticles supported on reduced graphene oxide for hydrolytic dehydrogenation of ammonia borane

RSC Advances ◽

10.1039/c3ra47023g ◽

2014 ◽

Vol 4 (27) ◽

pp. 13749-13752 ◽

Cited By ~ 89

Author(s):

Yuwen Yang ◽

Zhang-Hui Lu ◽

Yujuan Hu ◽

Zhujun Zhang ◽

Weimei Shi ◽

...

Keyword(s):

Graphene Oxide ◽

Catalytic Activity ◽

Reduced Graphene Oxide ◽

Copper Nanoparticles ◽

Ammonia Borane ◽

In Situ Synthesis ◽

Reduced Graphene

A facile in situ procedure has been successfully applied for synthesis of a RGO/Cu nanocomposite, which leads to the highest catalytic activity of Cu nanocatalysts up to now for the dehydrogenation of ammonia borane.

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Catalytic asymmetric hydrogenation reaction by in situ formed ultra-fine metal nanoparticles in live thermophilic hydrogen-producing bacteria

Nanoscale ◽

10.1039/d1nr00327e ◽

2021 ◽

Author(s):

Wei Bing ◽

Faming Wang ◽

Yuhuan Sun ◽

Jinsong Ren ◽

Xiaogang Qu

Keyword(s):

Metal Nanoparticles ◽

Catalytic Hydrogenation ◽

Asymmetric Hydrogenation ◽

Environmentally Friendly ◽

Hydrogenation Reaction ◽

Highly Efficient ◽

Hydrogenation Reactions ◽

Live Bacteria ◽

Catalytic Asymmetric Hydrogenation

An environmentally friendly biomimetic strategy has been presented and validated for the catalytic hydrogenation reaction in live bacteria. In situ formed ultra-fine metal nanoparticles can realize highly efficient asymmetric hydrogenation reactions.

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Si/Cu/C Nanohybrid Lithium-Ion Battery Anode with in Situ Incorporation of Nonagglomerated Super-Small Copper Nanoparticles Based on Epoxy Resin

Energy & Fuels ◽

10.1021/acs.energyfuels.0c04272 ◽

2021 ◽

Vol 35 (7) ◽

pp. 6250-6264

Author(s):

Kai Fang ◽

Liujia Ma ◽

Ya-Jun Cheng ◽

Senlin Xia ◽

Zhaohui Yang ◽

...

Keyword(s):

Epoxy Resin ◽

Lithium Ion Battery ◽

Copper Nanoparticles ◽

Lithium Ion ◽

Battery Anode

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Poly(N-isopropylacrylamide-co-methacrylic acid) microgel stabilized copper nanoparticles for catalytic reduction of nitrobenzene

Materials Science-Poland ◽

10.1515/msp-2015-0074 ◽

2015 ◽

Vol 33 (3) ◽

pp. 627-634 ◽

Cited By ~ 14

Author(s):

Zahoor H. Farooqi ◽

Zonarah Butt ◽

Robina Begum ◽

Shanza Rhauf Khan ◽

Ahsan Sharif ◽

...

Keyword(s):

Copper Nanoparticles ◽

Methacrylic Acid ◽

Catalytic Reduction ◽

Aqueous Media ◽

Activation Parameters ◽

Reducing Agent ◽

Different Temperatures ◽

Entropy Of Activation ◽

Micro Reactors

Abstract Poly(N-isopropylacrylamide-co-methacrylic acid) microgels [p(NIPAM-co-MAAc)] were synthesized by precipitation polymerization of N-isopropylacrylamide and methacrylic acid in aqueous medium. These microgels were characterized by dynamic light scattering and Fourier transform infrared spectroscopy. These microgels were used as micro-reactors for in situ synthesis of copper nanoparticles using sodium borohydride (NaBH4) as reducing agent. The hybrid microgels were used as catalysts for the reduction of nitrobenzene in aqueous media. The reaction was performed with different concentrations of catalyst and reducing agent. A linear relationship was found between apparent rate constant (kapp) and amount of catalyst. When the amount of catalyst was increased from 0.13 to 0.76 mg/mL then kapp was increased from 0.03 to 0.14 min-1. Activation parameters were also determined by performing reaction at two different temperatures. The catalytic process has been discussed in terms of energy of activation, enthalpy of activation and entropy of activation. The synthesized particles were found to be stable even after 14 weeks and showed catalytic activity for the reduction of nitrobenzene.

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