Continuous flow catalysis with CuBTC improves reaction time for synthesis of xanthene derivatives

Frontiers in Chemistry

Chemistry

Jonathan E. Thai¹  Melissa M. Reynolds²  Madeline C. Roach³ 

[1] Department of Chemistry, Colorado State University, Fort Collins, CO, United States;Department of Chemistry, Colorado State University, Fort Collins, CO, United States;School of Biomedical Engineering, Colorado State University, Fort Collins, CO, United States;Dapartment of Chemical and Biological Engineering, Colorado State University, Fort Collins, CO, United States;School of Biomedical Engineering, Colorado State University, Fort Collins, CO, United States;

关键词: metal-organic frameworks;    catalysis;    continuous flow;    flow catalysis;    xanthene;   

DOI  :  10.3389/fchem.2023.1259835

 received in 2023-07-16, accepted in 2023-10-04,  发布年份 2023

来源: Frontiers

【 摘 要 】

The copper-based metal-organic framework (MOF) CuBTC (where H3BTC = benzene-1,3,5-tricarboxylate) has been shown to be an efficient heterogeneous catalyst for the generation of 1,8-dioxo-octa-hydro xanthene derivatives, which are valuable synthetic targets for the pharmaceutical industry. We have applied this catalytic capability of CuBTC to a continuous flow system to produce the open chain form of 3,3,6,6-tetramethyl-9-phenyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione, a xanthene derivative from benzaldehyde and dimedone. An acid work-up after producing the open chain form of the xanthene derivative was used to achieve ring closure and form the final xanthene product. The CuBTC used to catalyze the reaction under continuous flow was confirmed to be stable throughout this process via analysis by SEM, pXRD, and FT-IR spectroscopy, elemental analysis, and XPS. The reaction to produce the open-chain form of the xanthene derivative produced an average yield of 33% ± 14% under the continuous flow (compared to 33% ± 0.12% of performing it under batch conditions). Based on the data obtained from this work, the continuous flow system required 22.5x less time to produce the desired xanthene derivative at comparable yields to batch reaction conditions. These results would allow for the xanthene derivative to be produced much faster, at a lower cost, and require less personal time while also removing the need to perform catalyst remove post reaction.

【 授权许可】

Unknown   
Copyright © 2023 Thai, Roach and Reynolds.