Thavarajah, Rumintha; Penny, Matthew R; Torii, Ryo; Hilton, Stephen T; (2023) Rapid Lewis Acid Screening and Reaction Optimization Using 3D-Printed Catalyst-Impregnated Stirrer Devices in the Synthesis of Heterocycles. The Journal of Organic Chemistry 10.1021/acs.joc.3c01601. (In press).

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Abstract

We describe the development of Lewis acid (LA) catalyst-impregnated 3D-printed stirrer devices and demonstrate their ability to facilitate the rapid screening of reaction conditions to synthesize heterocycles. The stereolithography 3D-printed stirrer devices were designed to fit round-bottomed flasks and Radleys carousel tubes using our recently reported solvent-resistant resin, and using CFD modeling studies and experimental data, we demonstrated that the device design leads to rapid mixing and rapid throughput over the device surface. Using a range of LA 3D-printed stirrers, the reaction between a diamine and an aldehyde was optimized for the catalyst and solvent, and we demonstrated that use of the 3D-printed catalyst-embedded devices led to higher yields and reduced reaction times. A library of benzimidazole and benzothiazole compounds were synthesized, and the use of devices led to efficient formation of the product as well as low levels of the catalyst in the resultant crude mixture. The use of these devices makes the process of setting up multiple reactions simpler by avoiding weighing out of catalysts, and the devices, once used, can be simply removed from the reaction, making the process of compound library synthesis more facile.

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