Dataset Information

Synthesis of CHF₂-Containing Heterocycles through Oxy-difluoromethylation Using Low-Cost 3D Printed PhotoFlow Reactors.

ABSTRACT: We report here a highly straightforward access to a variety of CHF₂-containing heterocycles, including lactones, tetrahydrofurans, tetrahydropyrans, benzolactones, phthalanes, and pyrrolidines, through a visible light-mediated intramolecular oxy-difluoromethylation under continuous flow. The method, which relies on the use of readily available starting materials, low-cost 3D printed photoflow reactors, and difluoromethyltriphenylphosphonium bromide used here as a CHF₂ radical precursor, is practical and scalable and provides the desired products in moderate to excellent yields and excellent regio- and stereoselectivities.

SUBMITTER: Zhang J

PROVIDER: S-EPMC11020168 | biostudies-literature | 2024 Apr

REPOSITORIES: biostudies-literature

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Publications

Synthesis of CHF2-Containing Heterocycles through Oxy-difluoromethylation Using Low-Cost 3D Printed PhotoFlow Reactors.

Zhang Jinlei J Selmi-Higashi Elias E Zhang Shen S Jean Alexandre A Hilton Stephen T ST Cambeiro Xacobe C XC Arseniyadis Stellios S

Organic letters 20240108 14

We report here a highly straightforward access to a variety of CHF2-containing heterocycles, including lactones, tetrahydrofurans, tetrahydropyrans, benzolactones, phthalanes, and pyrrolidines, through a visible light-mediated intramolecular oxy-difluoromethylation under continuous flow. The method, which relies on the use of readily available starting materials, low-cost 3D printed photoflow reactors, and difluoromethyltriphenylphosphonium bromide used here as a CHF2 radic ...[more]

PMID: 38190457

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Project description:Drug nanocrystals are a delivery system comprised of an active pharmaceutical ingredient, with small amounts of a surface stabilizer. Despite offering simplicity in formulation, their manufacture can be a challenging endeavour; this is especially true when the production is performed using microfluidic devices. Although precipitation within microchannels can lead to issues such as clogging, microfluidics is an appealing manufacturing method as it provides fine control over mixing conditions. This allows production of nanoparticles with a narrower size distribution and greater reproducibility compared to batch methods. To generate microfluidic devices cost effectively, replica moulding techniques are considered the manufacturing standard. Due to its simplicity and relatively low cost, 3D printing has become prevalent at the laboratory scale, especially during iterative development of new devices. A challenge of microfluidic-based methods is that they require specialized equipment and multi-step procedures, making them less accessible to users with no previous experience. In a recent study we developed a 3D printed flow-through reactor, referred to as reactor-in-a-centrifuge (RIAC). It is a simple device designed to fit in a 50 mL tube and actuated using a laboratory centrifuge, which removes the need for specialized instrumentation. The manufacturing capabilities of the RIAC have been already proven, by reproducible production of liposomes and silver nanoparticles. The present work demonstrates the use of RIACs with a straight- and spiral-shaped channel architecture to produce quercetin nanocrystals, with therapeutically relevant size (190-302 nm) and very low size dispersity (polydispersity index, PDI < 0.1). The work focused on evaluating how changes in operational parameters (actuation speed) and formulation components (medium viscosity and stabilizer type), impacted on nanocrystal size and PDI. Under all tested conditions the obtained nanocrystals had a smaller size and narrower size distribution, when compared to those produced with alternative methods. The obtained quercetin nanosuspensions however showed limited stability, which should be addressed in future investigations. The simplicity of the RIAC makes it an appealing technology to research groups, especially in low-resource settings and without prior expertise in microfluidics.

Dataset Information

Synthesis of CHF₂-Containing Heterocycles through Oxy-difluoromethylation Using Low-Cost 3D Printed PhotoFlow Reactors.

Publications

Synthesis of CHF<sub>2</sub>-Containing Heterocycles through Oxy-difluoromethylation Using Low-Cost 3D Printed PhotoFlow Reactors.

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