Sunflow: Sunlight Drives Fast and Green Photochemical Flow Reactions in Simple Microcapillary Reactors – Application to Photoredox and H‐Atom‐Transfer Chemistry

Nauth, Aaron; Lipp, Alexander; Lipp, Benjamin; Opatz, Till

doi:10.1002/ejoc.201601394

Cited by 37 publications

(27 citation statements)

References 55 publications

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“…Contrary to the above-mentioned examples, Opatz et al used sunlight instead of artificial irradiation from LED arrays. [37] AF EP capillary (25 m, approx. 20 mL) was braided and stabilized along aw ire netting, which also prevented self-shadowing of the capillary.T he reactor was directly oriented to the sun and repositioned every hourf or maximums olar radiation on sunny and non-hazy days between May and August in Mainz, Germany.W ith this setup, several substrates were screened for the oxidative cyanation of tertiarya mines.…”

Section: Cyanationmentioning

confidence: 99%

“…The last example in this sectioni sa boutt he cerium-based photocatalyzed functionalization of low molecular weight alkanes. [43] Zuo et al use hydrocarbonso fC 1 to C 4 structuref or alkylation and arylationr eactions as well as for amination with di-tert-butyl azodicarboxylate (37). The principle behind this approachi st he formation of cerium(IV)-alkoxides with, for example,C l 3 CCH 2 OH, which are activated by visible light resulting in Ce III species and alkoxyr adicals.…”

Section: Hydrogen Atom Transfer (Hat) Reactionsmentioning

confidence: 99%

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Flow Photochemistry as a Tool in Organic Synthesis

Rehm

2020

Chemistry A European J

109

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Photochemical transformations of molecular building blocks have become an important and widely recognized research field in the past decade. Detailed and deep understanding of novel photochemical catalysts and reaction concepts with visible light as the energy source has enabled a broad application portfolio for synthetic organic chemistry. In parallel, continuous‐flow chemistry and microreaction technology have become the basis for thinking and doing chemistry in a novel fashion with clear focus on improved process control for higher conversion and selectivity. As can be seen by the large number of scientific publications on flow photochemistry in the recent past, both research topics have found each other as exceptionally well‐suited counterparts with high synergy by combining chemistry and technology. This review will give an overview on selected reaction classes, which represent important photochemical transformations in synthetic organic chemistry, and which benefit from mild and defined process conditions by the transfer from batch to continuous‐flow mode.

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Section: Cyanationmentioning

confidence: 99%

Section: Hydrogen Atom Transfer (Hat) Reactionsmentioning

confidence: 99%

Flow Photochemistry as a Tool in Organic Synthesis

Rehm

2020

Chemistry A European J

109

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“…In the latter case, the use of the abundant chromium instead of the common ruthenium‐ or iridium‐based sensitizers provides an ecological and economical benefit. Photoorganocatalytic protocols were developed as well as an inexpensive and simple flow reactor using sunlight …”

Section: Selected Examples Of Routes To α‐Aminonitrilesmentioning

confidence: 99%

‐Aminonitriles: From Sustainable Preparation to Applications in Natural Product Synthesis

Grundke

Vierengel

Opatz

2020

The Chemical Record

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Due to their numerous reactivity modes, α‐aminonitriles represent versatile and valuable building blocks in organic total synthesis. Since their discovery by Adolph Strecker in 1850, this compound class has seen a wide dissemination in synthetic applications from laboratory to million‐ton industrial scale and was extensively used in the syntheses of various classes of natural products. As these compounds provide a multitude of reactivity options, we feel that a broad overview of their multiple reaction modes may reveal less familiar opportunities for successful total synthesis planning. This personal account article will thus focus on α‐aminonitriles used as key intermediates in selected natural product synthesis sequences which have been reported in the two decades since Enders’ and Shilvock's seminal review. Natural α‐aminonitriles will also briefly be treated.

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“…Almost all of them make use of solar concentrating devices to increase the photon flux toward the irradiated capillary or tube. The only exception in this regard is constituted by the Sunflow reactor [20], that instead employed a long capillary (25 m of FEP) to increase the solar-collecting area.…”

Section: Reactor Designsmentioning

confidence: 99%

“…Recently, Opatz and co-workers reported a novel reactor for solar photoredox and H-atom transfer chemistry named “sunflow” [20]. Compared to the reactors previously described, the sunflow is simpler as it does not include any type of solar concentration.…”

Section: Reactor Designsmentioning

confidence: 99%

Solar Photochemistry in Flow

Cambié

Noël

2018

Top Curr Chem (Z)

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In recent years, photochemistry has been a highly active research field. This renaissance is linked to the upsurge of photoredox catalysis, a versatile platform for synthetic methodologies using visible light photons as a traceless reagent. In contrast with UV, visible light constitutes almost half of the ground solar irradiance, making the use of solar light in chemistry a sustainable and viable possibility. However, the direct use of sunlight to power chemical reactions is still little explored. This can be explained by both the hurdles associated with solar radiation (e.g., its variability, irreproducibility, high IR content, etc.) and the need for a specialized photoreactor. Most of these issues can be tackled with technological solutions, and especially with the recourse to flow chemistry. Flow chemistry goes hand in hand with photochemistry thanks to the uniform irradiation it provides to the reaction. Furthermore, a continuous-flow reactor can be easily integrated with different solar collectors (including compound parabolic concentrators and luminescent solar concentrators) and constitutes the most efficient approach to solar photochemistry. After a description of the characteristics of the solar radiation relevant to chemistry, this chapter critically describes the different type of solar photoreactors and their applications in synthetic organic chemistry. Finally, an outlook on the future of solar photochemistry in flow is included.

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Sunflow: Sunlight Drives Fast and Green Photochemical Flow Reactions in Simple Microcapillary Reactors – Application to Photoredox and H‐Atom‐Transfer Chemistry

Abstract: "Sunflow" -The combination of a microcapillary reactor in continuous flow mode with sunlight as the most sustainable energy source imaginable was applied to a range of

Cited by 37 publications

References 55 publications

Flow Photochemistry as a Tool in Organic Synthesis

Flow Photochemistry as a Tool in Organic Synthesis

‐Aminonitriles: From Sustainable Preparation to Applications in Natural Product Synthesis

Solar Photochemistry in Flow

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