Electrocatalysis as an enabling technology for organic synthesis

Chemical Society Reviews, Год журнала: 2021, Номер 50(14), С. 7941 - 8002

Опубликована: Янв. 1, 2021

Electrochemistry has recently gained increased attention as a versatile strategy for achieving challenging transformations at the forefront of synthetic organic chemistry. Electrochemistry's unique ability to generate highly reactive radical and ion intermediates in controlled fashion under mild conditions inspired development number new electrochemical methodologies preparation valuable chemical motifs. Particularly, recent developments electrosynthesis have featured an use redox-active electrocatalysts further enhance control over selective formation downstream reactivity these intermediates. Furthermore, electrocatalytic mediators enable proceed manner that is mechanistically distinct from purely methods, allowing subversion kinetic thermodynamic obstacles encountered conventional synthesis. This review highlights key innovations within past decade area electrocatalysis, with emphasis on mechanisms catalyst design principles underpinning advancements. A host oxidative reductive are discussed grouped according classification transformation nature electrocatalyst.

Язык: Английский

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Organic Electrochemistry: Molecular Syntheses with Potential

ACS Central Science, Год журнала: 2021, Номер 7(3), С. 415 - 431

Опубликована: Март 9, 2021

Efficient and selective molecular syntheses are paramount to

Язык: Английский

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Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 2752 - 2906

Опубликована: Авг. 10, 2021

Photoinduced chemical transformations have received in recent years a tremendous amount of attention, providing plethora opportunities to synthetic organic chemists. However, performing photochemical transformation can be quite challenge because various issues related the delivery photons. These challenges barred widespread adoption steps industry. past decade, several technological innovations led more reproducible, selective, and scalable photoinduced reactions. Herein, we provide comprehensive overview these exciting advances, including flow chemistry, high-throughput experimentation, reactor design scale-up, combination photo- electro-chemistry.

Язык: Английский

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Powering the Future: How Can Electrochemistry Make a Difference in Organic Synthesis?

Chem, Год журнала: 2020, Номер 6(10), С. 2484 - 2496

Опубликована: Сен. 24, 2020

Язык: Английский

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New Redox Strategies in Organic Synthesis by Means of Electrochemistry and Photochemistry

ACS Central Science, Год журнала: 2020, Номер 6(8), С. 1317 - 1340

Опубликована: Июль 16, 2020

As the breadth of radical chemistry grows, new means to promote and regulate single-electron redox activities play increasingly important roles in driving modern synthetic innovation. In this regard, photochemistry electrochemistry-both considered as niche fields for decades-have seen an explosive renewal interest recent years gradually have become a cornerstone organic chemistry. Outlook article, we examine current state-of-the-art areas electrochemistry photochemistry, well nascent area electrophotochemistry. These techniques employ external stimuli activate molecules imbue privileged control reaction progress selectivity that is challenging traditional chemical methods. Thus, they provide alternative entries known reactive intermediates enable distinct strategies were previously unimaginable. Of many hallmarks, electro- are often classified "green" technologies, promoting reactions under mild conditions without necessity potent wasteful oxidants reductants. This reviews most growth these with special emphasis on conceptual advances given rise enhanced accessibility tools trade.

Язык: Английский

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Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 2487 - 2649

Опубликована: Ноя. 9, 2021

Redox processes are at the heart of synthetic methods that rely on either electrochemistry or photoredox catalysis, but how do and catalysis compare? Both approaches provide access to high energy intermediates (e.g., radicals) enable bond formations not constrained by rules ionic 2 electron (e) mechanisms. Instead, they 1e mechanisms capable bypassing electronic steric limitations protecting group requirements, thus enabling chemists disconnect molecules in new different ways. However, while providing similar intermediates, differ several physical chemistry principles. Understanding those differences can be key designing transformations forging disconnections. This review aims highlight these similarities between comparing their underlying principles describing impact electrochemical photochemical methods.

Язык: Английский

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Synthetic Photoelectrochemistry

Angewandte Chemie International Edition, Год журнала: 2019, Номер 59(29), С. 11732 - 11747

Опубликована: Дек. 5, 2019

Photoredox catalysis (PRC) and synthetic organic electrochemistry (SOE) are often considered competing technologies in synthesis. Their fusion has been largely overlooked. We review state-of-the-art photoelectrochemistry, grouping examples into three categories: 1) electrochemically mediated photoredox (e-PRC), 2) decoupled photoelectrochemistry (dPEC), 3) interfacial (iPEC). Such synergies prove beneficial not only for "greenness" chemical selectivity, but also the accumulation of energy accessing super-oxidizing or -reducing single electron transfer (SET) agents. Opportunities challenges this emerging exciting field discussed.

Язык: Английский

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Multi‐Photon Excitation in Photoredox Catalysis: Concepts, Applications, Methods

Angewandte Chemie International Edition, Год журнала: 2020, Номер 59(26), С. 10266 - 10284

Опубликована: Янв. 16, 2020

Abstract The energy of visible photons and the accessible redox potentials common photocatalysts set thermodynamic limits to photochemical reactions that can be driven by traditional visible‐light irradiation. UV excitation damaging induce side reactions, hence or even near‐IR light is usually preferable. Thus, photochemistry currently faces two divergent challenges, namely desire perform ever more thermodynamically demanding with increasingly lower photon energies. pooling low‐energy address both challenges simultaneously, whilst multi‐photon spectroscopy well established, synthetic photoredox chemistry has only recently started exploit processes on preparative scale. Herein, we have a critical look at developed mechanistic concepts, discuss pertinent experimental methods, provide an outlook into possible future developments this rapidly emerging area.

Язык: Английский

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Recent advances in visible light-activated radical coupling reactions triggered by (i) ruthenium, (ii) iridium and (iii) organic photoredox agents

Chemical Society Reviews, Год журнала: 2021, Номер 50(17), С. 9540 - 9685

Опубликована: Янв. 1, 2021

Visible light-activated reactions continue to expand and diversify. The example shown here is a Birch reduction achieved by organophotoredox reagents.

Язык: Английский

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Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds

Chemical Society Reviews, Год журнала: 2020, Номер 50(2), С. 766 - 897

Опубликована: Дек. 22, 2020

Recent developments and future prospects of visible-light photocatalysis in the late-stage functionalization pharmaceuticals natural bioactive compounds.

Язык: Английский

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