Ambient Pressure Ir@Hal-Catalyzed Hydrogenation of Aryl Aldehydes, Ketones, and Phenol

Hamdi, Jumanah; Diehl, Brooke N.; Do, Jaehyeon; Trudell, Mark L.

doi:10.1021/acs.joc.2c03006

“…The authors have cited additional references within the Supporting Information. [32,62,64,[75][76][77][78][79][80][81][82][83][84][85][86][87]…”

Section: Supporting Informationmentioning

confidence: 99%

Selective Electrocatalytic Degradation of Ether‐Containing Polymers

Hsu,

Ball,

Oh

et al. 2023

Angew Chem Int Ed

2

0

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Leveraging electrochemistry to degrade robust polymeric materials has the potential to impact society's growing issue of plastic waste. Herein, we develop an electrocatalytic oxidative degradation of polyethers and poly(vinyl ethers) via electrochemically mediated hydrogen atom transfer (HAT) followed by oxidative polymer degradation promoted by molecular oxygen. We investigated the selectivity and efficiency of this method, finding our conditions to be highly selective for polymers with hydridic, electron‐rich C−H bonds. We leveraged this reactivity to degrade polyethers and poly(vinyl ethers) in the presence of polymethacrylates and polyacrylates with complete selectivity. Furthermore, this method made polyacrylates degradable by incorporation of ether units into the polymer backbone. We quantified degradation products, identifying up to 36 mol % of defined oxidation products, including acetic acid, formic acid, and acetaldehyde, and we extended this method to degrade a polyether‐based polyurethane in a green solvent. This work demonstrates a facile, electrochemically‐driven route to degrade polymers containing ether functionalities.

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Selective Electrocatalytic Degradation of Ether‐Containing Polymers

Hsu,

Ball,

Oh

et al. 2023

Angewandte Chemie

0

View full text Add to dashboard Cite

Leveraging electrochemistry to degrade robust polymeric materials has the potential to impact society's growing issue of plastic waste. Herein, we develop an electrocatalytic oxidative degradation of polyethers and poly(vinyl ethers) via electrochemically mediated hydrogen atom transfer (HAT) followed by oxidative polymer degradation promoted by molecular oxygen. We investigated the selectivity and efficiency of this method, finding our conditions to be highly selective for polymers with hydridic, electron‐rich C−H bonds. We leveraged this reactivity to degrade polyethers and poly(vinyl ethers) in the presence of polymethacrylates and polyacrylates with complete selectivity. Furthermore, this method made polyacrylates degradable by incorporation of ether units into the polymer backbone. We quantified degradation products, identifying up to 36 mol % of defined oxidation products, including acetic acid, formic acid, and acetaldehyde, and we extended this method to degrade a polyether‐based polyurethane in a green solvent. This work demonstrates a facile, electrochemically‐driven route to degrade polymers containing ether functionalities.

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Synthesis and Characterization of Cu@Hal, an Effective Heterogeneous Catalyst for Aqueous Multicomponent Azide‐Alkyne [3+2] Cycloaddition Reactions

Diehl,

Hamdi,

Do

et al. 2024

ChemNanoMat

0

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The synthesis of a nanocomposite material consisting of Cu nanoparticles encapsulated in halloysite nanotubes (Cu@Hal) was achieved by the reduction of Cu(NO3)2•3H2O with sodium ascorbate/sodium borohydride in an aqueous suspension of trisodium citrate and halloysite. The nanocomposite was found to be an effective heterogeneous catalyst for the multicomponent copper catalyzed azide‐alkyne cycloaddition reaction (CuAAC). A variety of terminal alkynes reacted with benzyl halides and sodium azide in the presence of Cu@Hal in water. In situ formation of the organic azides afforded the corresponding 1,4‐disubstituted 1,2,3‐triazoles regioselectivily, in good to excellent yields. The catalyst was easily recovered and recycled without loss of activity with low metal leaching.

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Ambient Pressure Ir@Hal-Catalyzed Hydrogenation of Aryl Aldehydes, Ketones, and Phenol

Cited by 4 publications

References 51 publications

Selective Electrocatalytic Degradation of Ether‐Containing Polymers

Selective Electrocatalytic Degradation of Ether‐Containing Polymers

Selective Electrocatalytic Degradation of Ether‐Containing Polymers

Synthesis and Characterization of Cu@Hal, an Effective Heterogeneous Catalyst for Aqueous Multicomponent Azide‐Alkyne [3+2] Cycloaddition Reactions

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