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

The copper-based metal-organic framework (MOF) CuBTC (where H(3)BTC = 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...

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Autores principales: Thai, Jonathan E., Roach, Madeline C., Reynolds, Melissa M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10613637/
https://www.ncbi.nlm.nih.gov/pubmed/37908233
http://dx.doi.org/10.3389/fchem.2023.1259835
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author Thai, Jonathan E.
Roach, Madeline C.
Reynolds, Melissa M.
author_facet Thai, Jonathan E.
Roach, Madeline C.
Reynolds, Melissa M.
author_sort Thai, Jonathan E.
collection PubMed
description The copper-based metal-organic framework (MOF) CuBTC (where H(3)BTC = 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.
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spelling pubmed-106136372023-10-31 Continuous flow catalysis with CuBTC improves reaction time for synthesis of xanthene derivatives Thai, Jonathan E. Roach, Madeline C. Reynolds, Melissa M. Front Chem Chemistry The copper-based metal-organic framework (MOF) CuBTC (where H(3)BTC = 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. Frontiers Media S.A. 2023-10-16 /pmc/articles/PMC10613637/ /pubmed/37908233 http://dx.doi.org/10.3389/fchem.2023.1259835 Text en Copyright © 2023 Thai, Roach and Reynolds. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Thai, Jonathan E.
Roach, Madeline C.
Reynolds, Melissa M.
Continuous flow catalysis with CuBTC improves reaction time for synthesis of xanthene derivatives
title Continuous flow catalysis with CuBTC improves reaction time for synthesis of xanthene derivatives
title_full Continuous flow catalysis with CuBTC improves reaction time for synthesis of xanthene derivatives
title_fullStr Continuous flow catalysis with CuBTC improves reaction time for synthesis of xanthene derivatives
title_full_unstemmed Continuous flow catalysis with CuBTC improves reaction time for synthesis of xanthene derivatives
title_short Continuous flow catalysis with CuBTC improves reaction time for synthesis of xanthene derivatives
title_sort continuous flow catalysis with cubtc improves reaction time for synthesis of xanthene derivatives
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10613637/
https://www.ncbi.nlm.nih.gov/pubmed/37908233
http://dx.doi.org/10.3389/fchem.2023.1259835
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