Accelerating Visible‐Light Photoredox Catalysis in Continuous‐Flow Reactors

Straathof, Natan J. W.; Noël, Timothy

doi:10.1002/9783527674145.ch13

Cited by 11 publications

(12 citation statements)

References 70 publications

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“…Similar to how ohmic drop impedes electrosynthesis, the Beer–Lambert–Bouguer law limits photochemical transformations (Figure 14). As the attenuation effect of photon transport—or absorption (A)—is proportional to the penetration depth (d), photochemical reactions only occur in a limited film (millimeter magnitude) on the outside of the reactor [208,209,210,211]. This limited transmittance of irradiation due to absorption results in extended reaction times, especially in batch.…”

Section: Discussionmentioning

confidence: 99%

“…Standard upscaling of batch reactions will decrease the surface-to-volume ratio, which in turn will lengthen reaction times to impractical scale and increase the probability of side reactions. Nonetheless, scale-up of photoredox catalyzed reactions is possible, as displayed in Section 2.10 [165,166] and elsewhere [209,210]. These issues can be circumvented by the same technology electrosynthesis uses to cope with ohmic drop.…”

Section: Discussionmentioning

confidence: 99%

“…These issues can be circumvented by the same technology electrosynthesis uses to cope with ohmic drop. Continuous-flow reactors have good surface-area-to-volume ratios and allow for more efficient irradiation of the reaction mixture opposed to a dimension-enlarging strategy for scale-up [208,209,210,211,212]. Scalability of electrochemical transformations is possible in batch (Section 2.10) as the addition of supporting electrolytes can counteract ohmic voltage drop.…”

Section: Discussionmentioning

confidence: 99%

See 2 more Smart Citations

Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis

2019

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This review provides an overview of synthetic transformations that have been performed by both electro- and photoredox catalysis. Both toolboxes are evaluated and compared in their ability to enable said transformations. Analogies and distinctions are formulated to obtain a better understanding in both research areas. This knowledge can be used to conceptualize new methodological strategies for either of both approaches starting from the other. It was attempted to extract key components that can be used as guidelines to refine, complement and innovate these two disciplines of organic synthesis.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis

2019

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“…Due to an imbalance of charges generated during irradiation oxidation states of the photoabsorber and cocatalysts might change and this can reduce their stability leading to leaching. Special strategies have to be developed in order to counteract photocorrosion, for example through doping [174] . Blocking of active sites by unwanted intermediates on the surface might be an issue, for example in photocatalytic methanol reforming.…”

Section: Photocatalysismentioning

confidence: 99%

A Perspective on Heterogeneous Catalysts for the Selective Oxidation of Alcohols

Najafishirtari

Ortega

Douthwaite

et al. 2021

Chemistry A European J

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Selective oxidation of higher alcohols using heterogeneous catalysts is an important reaction in the synthesis of fine chemicals with added value. Though the process for primary alcohol oxidation is industrially established, there is still a lack of fundamental understanding considering the complexity of the catalysts and their dynamics under reaction conditions, especially when higher alcohols and liquid-phase reaction media are involved. Additionally, new materials should be developed offering higher activity, selectivity, and stability. This can be achieved by unraveling the structure-performance correlations of these catalysts under reaction conditions. In this regard, researchers are encouraged to develop more advanced characterization techniques to address the complex interplay between the solid surface, the dissolved reactants, and the solvent. In this mini-review, we report some of the most important approaches taken in the field and give a perspective on how to tackle the complex challenges for different approaches in alcohol oxidation while providing insight into the remaining challenges.

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“…Flow chemistry is generally considered an ideal solution for upscaling photochemical reactions, , and numerous examples of contemporary photoredox methods have been demonstrated by the pharmaceutical industry . Photoredox-mediated sp 2 -sp 3 cross-coupling reactions have also been performed in continuous flow, with good yields and short residence times reported .…”

Section: Introductionmentioning

confidence: 99%

Upscaling Photoredox Cross-Coupling Reactions in Batch Using Immersion-Well Reactors

Grimm

Hauer

Schulte

et al. 2020

Org. Process Res. Dev.

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Herein we describe a straightforward approach for the scale-up of photoredox cross-coupling reactions from milligram to multigram scale using immersion-well batch reactors with minimal reoptimization of the reaction conditions. This approach can be applied to both homogeneous and, more significantly, heterogeneous reaction mixtures. Furthermore, we have used an immersion-well side-loop reactor to perform a reaction on a 400 mmol scale (86 g of aryl bromide).

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Accelerating Visible‐Light Photoredox Catalysis in Continuous‐Flow Reactors

Cited by 11 publications

References 70 publications

Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis

Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis

A Perspective on Heterogeneous Catalysts for the Selective Oxidation of Alcohols

Upscaling Photoredox Cross-Coupling Reactions in Batch Using Immersion-Well Reactors

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