Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

Bogdos, Michael K.; Pinard, Emmanuel; Murphy, John A.

doi:10.3762/bjoc.14.179

Cited by 109 publications

(45 citation statements)

References 82 publications

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“…They are available in only limited amounts within the Earth's crust. Some engineered organic dyes have achieved comparable efficiency to iridium-or ruthenium-based catalysts 17 , intensifying their use in photoredox protocols 8,18 . For example, the Nicewicz group designed an acridinium-based organic photocatalyst (Mes-Acr + , in Fig.…”

Section: Sustainable Catalysis For Valorisation Of Renewable Sourcesmentioning

confidence: 99%

“…alkylation, amination, halogenation, perfluoroalkylation). Photoredox methods have been used to install such small functionalities to directly influence the ADME-tox (absorption, distribution, metabolism, excretion, and toxicology) features of a lead candidate 7 , using non-toxic and readily available materials 8 . Within this context, the Britton group and Merck collaborated to develop a photocatalytic C-H fluorination method for the preparative provision of γ-fluoroleucine derivative 2, a key intermediate in the synthesis of Odanacatib, a promising lead structure for osteoporosis treatment (Fig.…”

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confidence: 99%

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Chemistry glows green with photoredox catalysis

2020

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Can organic chemistry mimic nature in efficiency and sustainability? Not yet, but recent developments in photoredox catalysis animated the synthetic chemistry field, providing greener opportunities for industry and academia. Light on sustainability Nature is the main inspiration for scientists when it comes to sustainability. In biology, plants use photosynthesis to convert raw materials (CO 2 and water) into chemical energy (carbohydrates), exploiting the energy of solar photons. Photosynthesis is the quintessence of sustainable chemical reactivity, and the pinnacle that Green Chemistry aims to reach. Perhaps, one step forward in this direction has been made by recent progress in photochemical methods, particularly photoredox catalysis 1. Working as aspiring leaves, these strategies generate reactive radicals by using the ability of coloured catalysts (transition metal complexes or organic dyes) to absorb visible light radiation and activate stable low-energy organic molecules through single-electron processes (oxidation or reduction). These open-shell intermediates have been used to design a variety of reactions, which are unattainable with classical ionic chemistry triggered by thermal activation. Importantly, photoredox catalysis has revitalised other areas of synthesis, such as radical chemistry and photochemistry, providing opportunities for reaction invention and improvement. This chemistry has been used to tackle longstanding challenges in medicinal chemistry 2 , natural product synthesis 3 , and more broadly, across the spectrum of organic chemistry and catalysis 1,4. Along with its synthetic advantages, photoredox catalysis has clear benefits for sustainability, fulfilling several principles of Green Chemistry 5. Light radiation is its primary energy source. Light is free, non-hazardous, and environmentally friendly (energy efficiency). Photons provide enough energy to achieve the desired reactivity, without the high temperatures or harsh conditions often required by thermal activation. The light-absorbing species (photocatalysts) can be used in low catalytic amounts (use of catalytic reagents). By reaching an electronically excited state, they trigger single-electron transfer (SET) events to or from inactive/stable substrates. This generates highly reactive species in a mild and controlled manner. This has two positive impacts on sustainability. First, one can use less reactive low-energy reagents, allowing less hazardous and safer synthetic routes and easier disposal of less toxic or polluting by-products. Second, photoredox catalysis can activate generally poor reactive moieties within molecules (e.g. C-H bonds), while showing heightened functional group tolerance. This makes photoredox catalysis invaluable for designing shorter synthetic routes with enhanced atom economy, using renewable feedstock materials. Revived opportunities for drug discovery All these features have attracted the attention of the chemical industry, which recognised the potential of photoredox strategies to achieve efficient an...

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Section: Sustainable Catalysis For Valorisation Of Renewable Sourcesmentioning

confidence: 99%

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confidence: 99%

Chemistry glows green with photoredox catalysis

2020

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“…Catalysis enables the formation of chemical bonds and the production of various commodities under energy saving and environmentally friendly modes. [1] Since the beginning of the Century, magnificent development of visible-light photoredox catalysis has been witnessed in various disciplines, including chemical synthesis, [2] medicine, [3] renewable energy sources, [4] and environmental engineering. [5] This is strongly attributed to its capacity of high atom efficiency through photocatalytic approaches.…”

Section: Introductionmentioning

confidence: 99%

Scalable and Recyclable Heterogeneous Organo‐photocatalysts on Cotton Threads for Organic and Polymer Synthesis

et al. 2020

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As a highly efficient and environmentally friendly technology to address the challenges of sustainable chemistry and engineering, heterogeneous visible-light photoredox catalysis has been of great potential in organic and polymer synthesis. Eosin Y (EY), one of the commonly used organo-photoredox catalysts, has been immobilized onto commercial cotton threads via a straightforward method and single-step coupling reaction to prepare a scalable and recyclable heterogeneous photocatalyst. The immobilized EY is capable of generating singlet oxygen for organic transformations (e. g. oxidation of thioethers) in the presence of molecular oxygen, and effectively catalysing visiblelight photoinduced electron/energy transfer À reversible addition À fragmentation chain transfer polymerizations of various functional monomers for the synthesis of well-defined polymers in diverse "green" solvents. Facile separation and recovery of the cotton thread supported EY enable the reuse of the catalyst over multiple reaction cycles with well-retained catalytic efficiency.

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“…In fact, photochemistry does not compete with classical organic chemistry but offers additional synthetic routes to chemists. Since the beginning of the 21st century, the development of visible-light photochemical reactions, as well as the availability of cheap, compact, and low-consumption irradiation setups, has renewed the interest in photoinduced reactions [6][7][8][9][10] and discarded the classical UV-based photochemistry requiring bulky and expensive irradiation setups. Parallel to this, the use of UV light additionally raised safety concerns connected with the dangers of the UV radiations so that alternatives are actively researched [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances on Visible Light Metal-Based Photocatalysts for Polymerization under Low Light Intensity

Dumur

2019

Catalysts

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In recent years, polymerization processes activated by light have attracted a great deal of interest due to the wide range of applications in which this polymerization technique is involved. Parallel to the traditional industrial applications ranging from inks, adhesives, and coatings, the development of high-tech applications such as nanotechnology and 3D-printing have given a revival of interest to this polymerization technique known for decades. To initiate a photochemical polymerization, the key element is the molecule capable to interact with light, i.e., the photoinitiator and more generally the photoinitiating system, as a combination of several components is often required to create the reactive species responsible for the polymerization process. With the aim of reducing the photoinitiator content while optimizing the polymerization yield and/or the polymerization speed, photocatalytic systems have been developed, enabling the photosensitizer to be regenerated during the polymerization process. In this review, an overview of the photocatalytic systems developed for polymerizations carried out under a low light intensity and visible light is provided. Over the years, a wide range of organometallic photocatalysts has been proposed, addressing both the polymerization efficiency and/or the toxicity, as well as environmental issues.

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Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

Cited by 109 publications

References 82 publications

Chemistry glows green with photoredox catalysis

Chemistry glows green with photoredox catalysis

Scalable and Recyclable Heterogeneous Organo‐photocatalysts on Cotton Threads for Organic and Polymer Synthesis

Recent Advances on Visible Light Metal-Based Photocatalysts for Polymerization under Low Light Intensity

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