Emerging Activation Modes and Techniques in Visible-Light-Photocatalyzed Organic Synthesis

Vos, Dries De; Gadde, Karthik; Maes, Bert U. W.

doi:10.1055/a-1946-0512

Cited by 20 publications

(13 citation statements)

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“…Our discovery of dual one-photon (visible) and two-photon (NIR) W(CNAr) 6 -mediated catalysis represents a promising avenue for continued exploration. , Metal complexes that possess large TPA cross-sections will likely find important applications in bioimaging and photodynamic therapy . By employing NIR irradiation with minimal scattering and deep penetration depths, it is possible to greatly enhance images of biological samples.…”

Section: Discussionmentioning

confidence: 99%

Electronic Structures and Photoredox Chemistry of Tungsten(0) Arylisocyanides

et al. 2023

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Section: Discussionmentioning

confidence: 99%

Electronic Structures and Photoredox Chemistry of Tungsten(0) Arylisocyanides

et al. 2023

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“…An excellent example of the confusion that can surround PRC mechanisms is found in the related areas of “conPET” (consecutive photoinduced electron transfer) and “electrochemically-mediated PRC” (e-PRC). , These are adaptations of the ‘standard’ PRC mechanism that have both attracted particularly intense interest in recent years as they allow the catalysts employed to generate extremely reducing (or oxidizing) potentials that exceed those normally accessible in visible light PRC (though there is no strict limit, potentials beyond ca. ±2 V vs SCE are commonly considered difficult to achieve for standard PRC) . This allows for the facile activation of challenging, inert substrates, such as reduction of electron-neutral (or even electron-rich) aryl bromides and chlorides .…”

Section: Introductionmentioning

confidence: 99%

Shining Fresh Light on Complex Photoredox Mechanisms through Isolation of Intermediate Radical Anions

et al. 2023

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Photoredox catalysis (PRC) has gained enormous and wide-ranging interest in recent years but has also been subject to significant mechanistic uncertainty, even controversy. To provide a method by which the missing understanding can begin to be filled in, we demonstrate herein that it is possible to isolate as authentic materials the one-electron reduction products of representative PRC catalysts (PCs). Specifically, KC 8 reduction of both 9,10-dicyanoanthracene and a naphthalene monoamide derivative in the presence of a cryptand provides convenient access to the corresponding [K(crypt) + ][PC •− ] salts as clean materials that can be fully characterized by techniques including EPR and XRD. Because PC •− states are key intermediates in PRC reactions, such isolation allows for highly controlled study of these anions' specific reactivity and hence their mechanistic roles. As a demonstration of this principle, we show that these salts can be used to conveniently interrogate the mechanisms of recent, high-profile "conPET" and "e-PRC" reactions, which are currently the subject of both significant interest and acute controversy. Using very simple experiments, we are able to provide striking insights into these reactions' underlying mechanisms and to observe surprising levels of hidden complexity that would otherwise have been very challenging to identify and that emphasize the care and control that are needed when interrogating and interpreting PRC mechanisms. These studies provide a foundation for the study of a far broader range of questions around conPET, e-PRC, and other PRC reaction mechanisms in the future, using the same strategy of PC •− isolation.

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“…Furthermore, it lays the foundation for a second review, detailing lesser-known activation modes and some emerging concepts within the field of photocatalysis. 18…”

Section: K Gadde Et Almentioning

confidence: 99%

“…Particularly aimed at non-experts, the basic concepts introduced herein should prepare the reader for a discussion of advanced activation modes and some specialized emerging techniques within the field of photocatalysis, separately discussed in another review. 18 An in-Scheme 2 UV-light-mediated cycloaddition reactions and Norrish type I and II cleavage: SDS = sodium dodecyl sulfate This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.…”

Section: Review Synthesismentioning

confidence: 99%

“…Particularly aimed at non-experts, the basic concepts introduced herein should prepare the reader for a discussion of advanced activation modes and some specialized emerging techniques within the field of photocatalysis, separately discussed in another review. 18 An in-depth discussion of the (extensive) literature illustrating applications of the activation modes is outside the scope of this review, and readers are directed to state-of-the-art reviews and books on these specialized topics.…”

Section: Introductionmentioning

confidence: 99%

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Basic Concepts and Activation Modes in Visible-Light-Photocatalyzed Organic Synthesis

Gadde¹,

Vos²,

Maes³

2022

Synthesis

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Visible-light photocatalysis has established itself as a promising sustainable and powerful strategy to access reactive intermediates, i.e. radicals and radical ions, under mild reaction conditions using visible light irradiation. This field enables the development of formerly challenging or even previously inaccessible organic transformations. In this tutorial review, an overview of the essential concepts and techniques of visible light-mediated chemical processes and the most common types of photochemical activation of organic molecules, i.e. photoredox catalysis and photosensitization, are discussed. Selected photocatalytic alkene functionalization reactions are included as examples to illustrate the basic concepts and techniques with particular attention given to the understanding of their reaction mechanisms.

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Emerging Activation Modes and Techniques in Visible-Light-Photocatalyzed Organic Synthesis

Cited by 20 publications

References 174 publications

Electronic Structures and Photoredox Chemistry of Tungsten(0) Arylisocyanides

Electronic Structures and Photoredox Chemistry of Tungsten(0) Arylisocyanides

Shining Fresh Light on Complex Photoredox Mechanisms through Isolation of Intermediate Radical Anions

Basic Concepts and Activation Modes in Visible-Light-Photocatalyzed Organic Synthesis

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