Continuous flow photocyclization of stilbenes – scalable synthesis of functionalized phenanthrenes and helicenes

Lefebvre, Quentin; Jentsch, Marc; Rueping, Magnus

doi:10.3762/bjoc.9.221

Cited by 37 publications

(16 citation statements)

References 31 publications

(20 reference statements)

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“…The popular capillary photomicroreactor assembly was used for a variety of photocyclizations, such as the synthesis of pyridocarbazole ligands,65 phenanthrenes and helicenes,66 and tetrahydroquinolines 67. The same design was also used for the scalable photobromination of 5‐methylpyrimidine in flow to yield 5‐bromomethylpyrimidine, a precursor of Rosuvastatin 68.…”

Section: Photochemistry In Continuous‐flow Reactorsmentioning

confidence: 99%

Photochemical Transformations Accelerated in Continuous‐Flow Reactors: Basic Concepts and Applications

Straathof

Hessel

et al. 2014

Chemistry A European J

451

271

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Continuous-flow photochemistry is used increasingly by researchers in academia and industry to facilitate photochemical processes and their subsequent scale-up. However, without detailed knowledge concerning the engineering aspects of photochemistry, it can be quite challenging to develop a suitable photochemical microreactor for a given reaction. In this review, we provide an up-to-date overview of both technological and chemical aspects associated with photochemical processes in microreactors. Important design considerations, such as light sources, material selection, and solvent constraints are discussed. In addition, a detailed description of photon and mass-transfer phenomena in microreactors is made and fundamental principles are deduced for making a judicious choice for a suitable photomicroreactor. The advantages of microreactor technology for photochemistry are described for UV and visible-light driven photochemical processes and are compared with their batch counterparts. In addition, different scale-up strategies and limitations of continuous-flow microreactors are discussed.

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Section: Photochemistry In Continuous‐flow Reactorsmentioning

confidence: 99%

Photochemical Transformations Accelerated in Continuous‐Flow Reactors: Basic Concepts and Applications

Straathof

Hessel

et al. 2014

Chemistry A European J

451

271

View full text Add to dashboard Cite

show abstract

“…Their photophysical and chiroptical properties have been also investigated [21][22][23][24][25]. The [4]helicene skeleton demonstrate various applications such as molecular motor, building blocks for highly conjugated structures as well as larger [n]helicenes that have proved successful as chiral catalysts and ligands in asymmetric synthesis [26][27][28][29][30][31][32][33] and as blue emitters in OLEDs [34][35].…”

Section: Accepted Manuscriptmentioning

confidence: 99%

New [4]helicene derivatives: Synthesis, characterization and photophysical properties

Hafedh

Aloui

Raouafi

et al. 2018

Journal of Molecular Liquids

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The design and synthesis of new [4]helicene derivatives were carried out by incorporating well-defined electron donor and acceptor groups at selected positions of the aromatic nuclei, aiming to use them in optical applications. Helicenes have been obtained in good overall yields through a five-step sequence involving mild experimental conditions and easy purification. Photophysical properties of these tetracyclic systems have been evaluated by UV-visible absorption and fluorescence spectroscopies and an emission in the visible region was observed.

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“…Continuous-flow oxidative photocyclisation of stilbenes leads to a scaleable process for the preparation of polyanthrenes and helicenes. [59] This is indicated in the general Scheme 32, whereby a 150 W UV lamp provides irradiation to a wrapped UV-transparent ethylene propylene copolymer capillary (FEP) tube through which a solution of the stilbene and iodine passes to generate the product. The set-up readily facilitated solvent, flow rate and additive screening to afford optimum yields of products.…”

Section: Synthesis Of Thiophenes and Polycyclic Aromatic Hydrocarbonsmentioning

confidence: 99%

Flow Chemistry Meets Advanced Functional Materials

Myers

Fitzpatrick

Turner

et al. 2014

Chemistry A European J

120

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Flow chemistry and continuous processing techniques are beginning to have a profound impact on the production of functional materials ranging from quantum dots, nanoparticles and metal organic frameworks to polymers and dyes. These techniques provide robust procedures which not only enable accurate control of the product material's properties but they are also ideally suited to conducting experiments on scale. The modular nature of flow and continuous processing equipment rapidly facilitates reaction optimisation and variation in function of the products.

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Continuous flow photocyclization of stilbenes – scalable synthesis of functionalized phenanthrenes and helicenes

Abstract: SummaryA continuous flow oxidative photocyclization of stilbene derivatives has been developed which allows the scalable synthesis of backbone functionalized phenanthrenes and helicenes of various sizes in good yields.

Cited by 37 publications

References 31 publications

Photochemical Transformations Accelerated in Continuous‐Flow Reactors: Basic Concepts and Applications

Photochemical Transformations Accelerated in Continuous‐Flow Reactors: Basic Concepts and Applications

New [4]helicene derivatives: Synthesis, characterization and photophysical properties

Flow Chemistry Meets Advanced Functional Materials

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