Electrochemically Driven C−H Hydrogen Abstraction Processes with the Tetrachloro‐Phthalimido‐N‐Oxyl (Cl<sub>4</sub>PINO) Catalyst

Buckingham, Mark A.; Cunningham, W. B.; Bull, Steven D.; Buchard, Antoine; Folli, Andrea; Murphy, D. M.; Marken, Frank

doi:10.1002/elan.201800147

Cited by 6 publications

(4 citation statements)

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“…The investigations of NHPI derivatives for the functionalization of organic molecules have been presented in many reports. For example, 3-CH 3 O-NHPI, , 4-CH 3 O-NHPI, ,− 4-CH 3 -NHPI, − 3-F-NHPI, − 4-Cl-NHPI, 4,5-diCl-NHPI, and F 4 -NHPI have ben successfully tested in the processes of oxidation of alcohols under aerobic, laccase-catalyzed, , and electrochemical oxidation conditions. , Cl 4 -NHPI demonstrated a high potential as a catalyst for electrochemical C–H oxidation of allylic compounds and primary and secondary alcohols. , The observed electrochemical reactivity of NHPI catalysts is determined by their redox potential and does not correlate with their reactivity under conditions of aerobic catalytic or laccase oxidation. The decomposition of the electrogenerated PINO radical is the limiting factor in the development of electrochemical oxidation processes…”

Section: Resultsmentioning

confidence: 99%

“…10a,12b Cl 4 -NHPI demonstrated a high potential as a catalyst for electrochemical C−H oxidation of allylic compounds 12b and primary and secondary alcohols. 10a, 29 The observed electrochemical reactivity of NHPI catalysts is determined by their redox potential and does not correlate with their reactivity under conditions of aerobic catalytic or laccase oxidation. The decomposition of the electrogenerated PINO radical is the limiting factor in the development of electrochemical oxidation processes.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Kinetics of N-oxyl Radicals’ Decay

et al. 2020

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N-oxyl radicals of various structures were generated by oxidation of corresponding N-hydroxy compounds with iodobenzene diacetate, [bis(trifluoroacetoxy)]iodobenzene, and ammonium cerium(IV) nitrate in acetonitrile. The decay rate of N-oxyl radicals follows first-order kinetics and depends on the structure of N-oxyl radicals, reaction conditions, and the nature of the solvent and oxidant. The values of the self-decay constants change within 1.4 × 10 −4 s −1 for the 3,4,5,6-tetraphenylphthalimide-N-oxyl radical to 1.4 × 10 −2 s −1 for the 1-benzotriazole-N-oxyl radical. It was shown that the rate constants of the phthalimide-N-oxyl radicalsʼ self-decay with different electron-withdrawing or -donor substituents in the benzene ring are higher than that of the unsubstituted phthalimide-N-oxyl radical in most cases. The solvent effect on the process of phthalimide-N-oxyl radical self-decomposition was investigated. The dependence of the rate constants on the Gutmann donor numbers was shown.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Kinetics of N-oxyl Radicals’ Decay

et al. 2020

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“…the basis for simulating larger systems that creates I4.0. Simulation in this part includes Finite Element Analysis (FEA) [69], simulation of acoustics performance of the product [70,71] simulation of composites structures behavior and the progressive degradation [72,73] and fluid dynamics simulation [74] can be distinguished. One of process simulation challenges is the development of Computer Aided Manufacturing (CAM) to automate a manufacturing process [75].…”

Section: E41 Product and Processes: Product And Processes Simulatiomentioning

confidence: 99%

Mapping Industry 4.0 Enabling Technologies into United Nations Sustainability Development Goals

et al. 2021

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The emerging of the fourth industrial revolution, also known as Industry 4.0 (I4.0), from the advancement in several technologies is viewed not only to promote economic growth, but also to enable a greener future. The 2030 Agenda of the United Nations for sustainable development sets out clear goals for the industry to foster the economy, while preserving social well-being and ecological validity. However, the influence of I4.0 technologies on the achievement of the Sustainable Development Goals (SDG) has not been conclusively or systematically investigated. By understanding the link between the I4.0 technologies and the SDGs, researchers can better support policymakers to consider the technological advancement in updating and harmonizing policies and strategies in different sectors (i.e., education, industry, and governmental) with the SDGs. To address this gap, academic experts in this paper have investigated the influence of I4.0 technologies on the sustainability targets identified by the UN. Key I4.0 element technologies have been classified to enable a quantitative mapping with the 17 SDGs. The results indicate that the majority of the I4.0 technologies can contribute positively to achieving the UN agenda. It was also found that the effects of the technologies on individual goals varies between direct and strong, and indirect and weak influences. The main insights and lessons learned from the mapping are provided to support future policy.

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“…The KIE experiment for the Cl4NHPI-based catalytic system (oxidation reactions of a range of primary, secondary, andcyclic alcohols) has been investigated by Buckingham et al [105] and turned out that the C−H hydrogen abstraction process is the rate determining step for the reaction.…”

Section: Suggested Mechanismmentioning

confidence: 99%

Visible Light-Mediated Metal-Free Photocatalytic Oxidative Reactions and Cycloadditions

Zhang

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He always shares his ideas and discusses with me about the projects which sped up my projects a lot. I am very grateful to Prof. Dr. Konrad Koszinowski for his kindly accepting to be the second supervisor for my first two-year study and becomes my first supervisor in Göttingen during my joint PhD program study. He always gives me highly valuable suggestions and comments in last three years. I am also really appreciated for his kind corrections, suggestions, and polish of my thesis. I benefited and learned much from his rigorous spirit. I deeply thank my lab colleagues Daniel Riemer, Waldemar Schilling, Jiri Kollmann, Tong Zhang, Shaowei Qin, Nareh Hatami, Prakash Sahoo etc. for their kind help during my PhD study. I am also appreciated for the kind help of Prof. Dr. Maes and all ORSY members during the study in the University of Antwerp. I would like to thank the analytical departments especially the Dr. Michael John and Dr. Holm Frauendorf at the IOBC, for their strong support and offered possibility to operate several machines by myself. I gratefully acknowledge China Scholarship Council (CSC) and BOF International Joint PhD Fellowships for the financial support during my research stay in Germany and Belgium. Special thanks should give to my wife, Mrs. Na Zhang who always encourages me to face and overcome challenges. She is always there for me. At last, I will thank my parents, sister and other families for their continuous support and encouragement. I love you all forever. Contents VIII UCNF nitrogen deficient carbon nitride VB valence band wt% weight by volume total solar irradiance is about 1366.1 W m -2 which provides roughly 4.3x10 20 J energyonly in 1 h. [4] Therefore, if it is harvested and utilized in organic transformations, could bring a vision to solve the sustainable issues.As a key factor in the recent rapid growth of this field has been recognized the fact that readily accessible metal complexes and organic dyes can facilitate the conversion of visible light into chemical energy under exceptionally mild conditions. Among them, ruthenium-and iridium-based organometallic complexes stand at the forefront of this class. These species are mostly employed as radical sources: they exhibit excellent visible-light absorption and long-lived excited states (Scheme 1.1). [5] Scheme 1.1 Chemical structures of typical homogeneous photocatalysts. [4a][6a] Even though these species are not strong oxidants or reductants in their ground states, in their excited state they are potent single electron transfer reagents with suitable redox potentials. The redox potential is a measure of the tendency of a chemical species to gain electrons from an electrode and thereby get reduced. In principle, a higher positive value of the redox potential signifies a greater affinity for electrons to be gained, thereby a higher tendency to be reduced. Hence, the redox potential of the photocatalyst must be matched to the reagents of the reaction. Compared to the transition metal complexes, metal-free organic dyes (e.g. eosin ...

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Electrochemically Driven C−H Hydrogen Abstraction Processes with the Tetrachloro‐Phthalimido‐N‐Oxyl (Cl₄PINO) Catalyst

Cited by 6 publications

References 37 publications

Kinetics of N-oxyl Radicals’ Decay

Kinetics of N-oxyl Radicals’ Decay

Mapping Industry 4.0 Enabling Technologies into United Nations Sustainability Development Goals

Visible Light-Mediated Metal-Free Photocatalytic Oxidative Reactions and Cycloadditions

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Electrochemically Driven C−H Hydrogen Abstraction Processes with the Tetrachloro‐Phthalimido‐N‐Oxyl (Cl4PINO) Catalyst

Cited by 6 publications

References 37 publications

Kinetics of N-oxyl Radicals’ Decay

Kinetics of N-oxyl Radicals’ Decay

Mapping Industry 4.0 Enabling Technologies into United Nations Sustainability Development Goals

Visible Light-Mediated Metal-Free Photocatalytic Oxidative Reactions and Cycloadditions

Contact Info

Product

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Electrochemically Driven C−H Hydrogen Abstraction Processes with the Tetrachloro‐Phthalimido‐N‐Oxyl (Cl₄PINO) Catalyst