Metal‐Free Visible‐Light‐Mediated Hydrotrifluoromethylation of Unactivated Alkenes and Alkynes in Continuous Flow

Barthelemy, Anne‐Laure; Dagousset, Guillaume; Magnier, Emmanuel

doi:10.1002/ejoc.201901252

Cited by 24 publications

(12 citation statements)

References 62 publications

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“…The use of fluorinated sulfilimino iminiums in a photocatalytic transformation in flow was described by Dagousset, Magnier, and co-workers (Scheme ). In a previous report in batch, the authors reported this class of compounds which provide perfluoroalkyl radical under light irradiation in the presence of an iridium(III) catalyst for the first time . In flow, fluorinated sulfilimino iminiums were used to hydroperfluoroalkylate alkynes and alkenes.…”

Section: Flow Photochemistrymentioning

confidence: 99%

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

et al. 2021

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

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Section: Flow Photochemistrymentioning

confidence: 99%

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

et al. 2021

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“…In addition, photochemical flow approaches have been developed with great success for functionalization reactions, such as halogenations [66][67][68][69], trifluoromethylations [70][71][72], oxygenations [73][74][75] and C-H activations [76][77][78]. All these applications showcase how continuous set-ups help to overcome limitations commonly encountered with classical photochemistry, and it is apparent that a variety of light sources as well as reactor configurations are exploited to best serve the intended chemical route.…”

Section: Remaining Challenges For Effectively Integrating Photoreactimentioning

confidence: 99%

Continuous Flow Photochemistry for the Preparation of Bioactive Molecules

2020

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The last decade has witnessed a remarkable development towards improved and new photochemical transformations in response to greener and more sustainable chemical synthesis needs. Additionally, the availability of modern continuous flow reactors has enabled widespread applications in view of more streamlined and custom designed flow processes. In this focused review article, we wish to evaluate the standing of the field of continuous flow photochemistry with a specific emphasis on the generation of bioactive entities, including natural products, drugs and their precursors. To this end we highlight key developments in this field that have contributed to the progress achieved to date. Dedicated sections present the variety of suitable reactor designs and set-ups available; a short discussion on the relevance of greener and more sustainable approaches; and selected key applications in the area of bioactive structures. A final section outlines remaining challenges and areas that will benefit from further developments in this fast-moving area. It is hoped that this report provides a valuable update on this important field of synthetic chemistry which may fuel developments in the future.

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“…The old Ciamiciamn reactions and their methodology had again become on the forefront of research with the advent of 'green' chemistry, where his methods have been found to fit easily with the requirements of that topic and have become a favorite ground for testing flow conditions [101][102][103][104][105][106][107] in microreactors and for photocatalytic processes including those involving visible light. Fig.…”

Section: Discussionmentioning

confidence: 99%

Norrish’ type I and II reactions and their role in the building of photochemical science

Albini

2021

Photochem Photobiol Sci

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The highly inspiring work by Professor Norrish has exerted a consistent influence on chemistry and, in particular, on photochemistry, where he was one of the first scientists, along with Gilbert N. Lewis, able to develop a viable concept of excited states and their rate of reaction. However, having him listed among the authors of two name reactions, known as Norrish Type I and Type II, plus a subcase of the latter that is the Yang cyclization, is not coherent. Indeed, Norrish had no interest in organic synthesis, while this is a required feature of name reactions. And, at any rate, Professors Ciamician and Paternò had arrived at the same conclusions with the same compounds much earlier, except for the measurement of quantum yields. Things are too long away now for introducing any change, but one should remember that using Norrish name here is a mistake, while it would be appropriate to add the name of Ciamician for a different name reaction, the 2 + 2 cycloaddition of alkenes and conjugated carbonyls. In 1968, such an attribution was proposed by Professor Schömberg, but this had no effect and the present assignment has become a habit. The most important thing, however, is that the 2 + 2 reaction has become one of the most popular reactions in synthetic photochemistry.

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Metal‐Free Visible‐Light‐Mediated Hydrotrifluoromethylation of Unactivated Alkenes and Alkynes in Continuous Flow

Cited by 24 publications

References 62 publications

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

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

Continuous Flow Photochemistry for the Preparation of Bioactive Molecules

Norrish’ type I and II reactions and their role in the building of photochemical science

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