Towards a Scalable Synthesis of 2‐Oxabicyclo[2.2.0]hex‐5‐en‐3‐one Using Flow Photochemistry

Williams, Jason D.; Otake, Yuma; Coussanes, Guilhem; Saridakis, Iakovos; Maulide, Nuno; Kappe, C. Oliver

doi:10.1002/cptc.201900017

Cited by 16 publications

(14 citation statements)

References 39 publications

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“…A limitation of this method is observed when tubing made of perfluorinated polymers is used under UV irradiation. This type of tubing is commonly used due to its flexibility and transparency, but prolonged exposure to UV might result in fouling (in turn lowering the transparency) [84][85][86] and/or mechanical damage [84], ultimately resulting in reaction inhibition or reactor replacement.…”

Section: Scale-up Strategies and Designsmentioning

confidence: 99%

Flow Photochemistry: Shine Some Light on Those Tubes!

Sambiagio

Noël

2020

Trends in Chemistry

313

223

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Continuous-flow chemistry has recently attracted significant interest from chemists in both academia and industry working in different disciplines and from different backgrounds. Flow methods are now being used in reaction discovery/methodology, in scale-up and production, and for rapid screening and optimization. Photochemical processes are currently an important research field in the scientific community and the recent exploitation of flow methods for these methodologies has made clear the advantages of flow chemistry and its importance in modern chemistry and technology worldwide. This review highlights the most important features of continuous-flow technology applied to photochemical processes and provides a general perspective on this rapidly evolving research field. Microflow Technology and Photochemistry: A Perfect MatchThe use of light to promote chemical reactions has been exploited since the 18th century, but only recently a resurgence has been observed in synthetic organic chemistry, in particular due to the development of visible-light photoredox catalysis [1-5]. All transformations involving light (e.g., Figure 1A-D) must consider, besides classical chemical parameters (i.e., reaction conditions), the photophysical aspects of the sensitizer (see Glossary)/photocatalyst (when used), and the reactor design. The latter, although often neglected by chemists, is a critical aspect for the outcome of the studied chemical transformation. This includes, for example, the size, shape, and material of the reaction vessel, the characteristics and positioning of the light source(s), and heat-transfer properties, particularly when high-intensity lamps are used [6,7]. The engineering and technological aspects of photochemical processes are often at the basis of the irreproducibility and non-scalability of such transformations.According to the Beer-Lambert law, light transmittance decreases exponentially with the distance from the light source ( Figure 1F). For a standard batch reactor (diameter at least in the centimeter range), light intensity decreases considerably from the flask walls to the middle of the reaction mixture, resulting in slow reactions and nonhomogeneous irradiation of the reaction mixture. Performing photochemical reactions in microchannels (ID < 1 mm) allows a higher and more homogeneous photon flux, resulting in shorter reaction times and consequently less side-product formation due to over-irradiation, often observed in batch [8,9]. Another advantage of microflow chemistry, correlated with the large surface:volume ratio, is improved heat and mass transfer, with the possibility to perform mass-transfer-limited multiphasic reactions efficiently [10]. Reactive chemicals and intermediates can be handled more safely in flow than in batch, as no accumulation of dangerous components occurs within the confined reactor volume due to the continuous nature of the process. Together, these result in often faster, safer, and higher-yielding reactions, with the possibility to perform reactions under condition...

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Section: Scale-up Strategies and Designsmentioning

confidence: 99%

Flow Photochemistry: Shine Some Light on Those Tubes!

Sambiagio

Noël

2020

Trends in Chemistry

313

223

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“…Their small size is also beneficial for homogeneous irradiation with small photon flux gradients, ensuring high reaction control for synthesis and mechanistic understanding [110] . In addition, these systems are ideal models for standardized operation, and they facilitate transfer of light‐driven processes to a technical scale [97, 111–113] …”

Section: Technical Parameters Affecting Catalytic Activitymentioning

confidence: 99%

Comparative Evaluation of Light‐Driven Catalysis: A Framework for Standardized Reporting of Data**

et al. 2022

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Light-driven homogeneous and heterogeneous catalysis require a complex interplay between light absorption, charge separation, charge transfer, and catalytic turnover. Optical and irradiation parameters as well as reaction engineering aspects play major roles in controlling catalytic performance. This multitude of factors makes it difficult to objectively compare light-driven catalysts and provide an unbiased performance assessment. This Scientific Perspective highlights the importance of collecting and reporting experimental data in homogeneous and heterogeneous light-driven catalysis. A critical analysis of the benefits and limitations of the commonly used experimental indicators is provided. Data collection and reporting according to FAIR principles is discussed in the context of future automated data analysis. The authors propose a minimum dataset as a basis for unified collecting and reporting of experimental data in homogeneous and heterogeneous light-driven catalysis. The community is encouraged to support the future development of this parameter list through an open online repository.

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“…Copyright (2019) American Chemical Society flow chemistry to improving the scalability of this reaction [42]. Careful optimisation of reaction conditions found the correct selection of light source to be of critical importance, with an improvement in yield being observed using a commercially available medium pressure mercury lamp (with the appropriate light filter) when compared to a weaker 8 W UV lamp emitting at 303 nm.…”

Section: Laboratory Scale (< 100 G/day)mentioning

confidence: 99%

Scalability of photochemical reactions in continuous flow mode

2021

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Continuous flow photochemistry as a field has witnessed an increasing popularity over the last decade in both academia and industry. Key drivers for this development are safety, practicality as well as the ability to rapidly access complex chemical structures. Continuous flow reactors, whether home-built or from commercial suppliers, additionally allow for creating valuable target compounds in a reproducible and automatable manner. Recent years have furthermore seen the advent of new energy efficient LED lamps that in combination with innovative reactor designs provide a powerful means to increasing both the practicality and productivity of modern photochemical flow reactors. In this review article we wish to highlight key achievements pertaining to the scalability of such continuous photochemical processes. Graphical abstract

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Towards a Scalable Synthesis of 2‐Oxabicyclo[2.2.0]hex‐5‐en‐3‐one Using Flow Photochemistry

Cited by 16 publications

References 39 publications

Flow Photochemistry: Shine Some Light on Those Tubes!

Flow Photochemistry: Shine Some Light on Those Tubes!

Comparative Evaluation of Light‐Driven Catalysis: A Framework for Standardized Reporting of Data**

Scalability of photochemical reactions in continuous flow mode

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