Renewable resources for sustainable metallaelectro-catalysed C–H activation

Samanta, Ramesh C.; Meyer, Tjark H.; Siewert, Inke; Ackermann, Lutz

doi:10.1039/d0sc03578e

Cited by 79 publications

(25 citation statements)

References 134 publications

(141 reference statements)

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“…Surpassing these shortcomings, the field of metallaelectrocatalysis has emerged. 36 , 40 , 131 − 133 Redox potentials can be adjusted continuously, for instance, by a potentiostat. This allows broader functional group tolerance and a decreased need for complex ligand systems.…”

Section: Modern Oxidation Strategiesmentioning

confidence: 99%

“…To access differing redox potentials, chemical modifications via resource-demanding, multistep synthesis are necessary. Surpassing these shortcomings, the field of metallaelectrocatalysis has emerged. ,,− Redox potentials can be adjusted continuously, for instance, by a potentiostat. This allows broader functional group tolerance and a decreased need for complex ligand systems.…”

Section: Modern Oxidation Strategiesmentioning

confidence: 99%

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C–H Activation: Toward Sustainability and Applications

2021

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Since the definition of the “12 Principles of Green Chemistry” more than 20 years ago, chemists have become increasingly mindful of the need to conserve natural resources and protect the environment through the judicious choice of synthetic routes and materials. The direct activation and functionalization of C–H bonds, bypassing intermediate functional group installation is, in abstracto , step and atom economic, but numerous factors still hinder the sustainability of large-scale applications. In this Outlook, we highlight the research areas seeking to overcome the sustainability challenges of C–H activation: the pursuit of abundant metal catalysts, the avoidance of static directing groups, the replacement of metal oxidants, and the introduction of bioderived solvents. We close by examining the progress made in the subfield of aryl C–H borylation from its origins, through highly efficient but precious Ir-based systems, to emerging 3d metal catalysts. The future growth of this field will depend on industrial uptake, and thus we urge researchers to strive toward sustainable C–H activation.

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Section: Modern Oxidation Strategiesmentioning

confidence: 99%

Section: Modern Oxidation Strategiesmentioning

confidence: 99%

C–H Activation: Toward Sustainability and Applications

2021

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“…It is without doubt that C-H bond activation chemistry has reached new heights in the advent of the new century. Researchers around the globe have devoted significant resources in advancing the field especially in the context of sustainable synthesis (Dalton et al, 2021;Samanta et al, 2020;Tzouras et al, 2017). There has been a surge in method development encompassing diverse techniques that would allow the rather difficult task of selectively activating C-H bonds in many different substrate classes and install new functionalities.…”

Section: Outlook and Future Perspectivementioning

confidence: 99%

An Introductory Overview of C–H Bond Activation/ Functionalization Chemistry with Focus on Catalytic C(sp3)–H Bond Borylation

Reyes

Sawamura

2021

KIMIKA

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The direct and selective functionalization of C–H bonds provides novel disconnections and innovative strategies to streamline the synthesis of molecules with diverse complexities. However, despite the significant advances in the elaboration of techniques for C–H activation, the utilization of unactivated C(sp3)–H bonds remains challenging. In particular, asymmetric transformation of C(sp3)–H bonds is underdeveloped owing to the lack of catalytic systems that can competently discriminate among ubiquitous C–H bonds in organic molecules. This short review aims to outline the challenges and strategies for the catalytic functionalization of C(sp3)–H bonds giving a general and non-exhaustive explanatory approach. Current strategies on the basis of the substrates and reaction mechanisms are summarized in Section 1. Examples of enantioselective C–H bond transformations are then given in Section 2. Finally, in Section 3, an outline of current methodologies towards the direct borylation of C(sp3)–H bonds is described to showcase the importance of developing techniques for catalytic C–H bond chemistry. While we try to cover all excellent reports available in the literature on this topic, any omissions are unintentional, taking note of the most representative examples available.

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“… 27 Here, electrons can be used as traceless redox equivalents to achieve exceptional selectivities, thus avoiding stoichiometric redox reagents and undesired byproduct generation. 28 The development of commercial electrochemical equipment, 29 has enabled most user-friendly access of electrosynthesis. Furthermore, the often exceedingly mild reaction conditions and the frequent use of protic solvents encompasses electrosynthesis as an environmentally benign strategy for molecular assembly.…”

Section: Introductionmentioning

confidence: 99%

Organic Electrochemistry: Molecular Syntheses with Potential

et al. 2021

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Efficient and selective molecular syntheses are paramount to inter alia biomolecular chemistry and material sciences as well as for practitioners in chemical, agrochemical, and pharmaceutical industries. Organic electrosynthesis has undergone a considerable renaissance and has thus in recent years emerged as an increasingly viable platform for the sustainable molecular assembly. In stark contrast to early strategies by innate reactivity, electrochemistry was recently merged with modern concepts of organic synthesis, such as transition-metal-catalyzed transformations for inter alia C–H functionalization and asymmetric catalysis. Herein, we highlight the unique potential of organic electrosynthesis for sustainable synthesis and catalysis, showcasing key aspects of exceptional selectivities, the synergism with photocatalysis, or dual electrocatalysis, and novel mechanisms in metallaelectrocatalysis until February of 2021.

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Renewable resources for sustainable metallaelectro-catalysed C–H activation

Abstract: The necessity for more sustainable industrial chemical processes has internationally been agreed upon. During the last decade, the scientific community has responded to this urgent need by developing novel sustainable...

Cited by 79 publications

References 134 publications

C–H Activation: Toward Sustainability and Applications

C–H Activation: Toward Sustainability and Applications

An Introductory Overview of C–H Bond Activation/ Functionalization Chemistry with Focus on Catalytic C(sp3)–H Bond Borylation

Organic Electrochemistry: Molecular Syntheses with Potential

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