Issue 17, 2024

Crystal facet-dependent upgrading of saccharides over barium peroxide to synthesize C-glycoside ketones

Abstract

Transformation of abundant and easily accessible carbohydrates to high-value chemicals is of the essence in the field of biorefinery. However, selective conversion of unprotected saccharides faces great challenges regarding the peculiarity of multi-functional groups. Herein, barium peroxide (BaO2) with a preferential crystal facet presented excellent performance in the direct Knoevenagel condensation of various saccharides with acetylacetone for the synthesis of C-glycoside ketones. Characterization methods including XRD, TG-DSC, Raman spectroscopy, SEM, and TEM revealed that commercial barium oxide (BaO) calcinated under an air atmosphere could react with oxygen to generate the new species of BaO2. Moreover, the relative proportion of each crystal facet of BaO2 could be controlled by regulating the calcination conditions. Also, BaO2 with the (110) facet exhibited better reactivity than that with the dominant (002) crystal facet. Combining the results from experimental studies and DFT calculations, it was revealed that the different adsorption energies of the substrates on diverse crystal facets could modulate the reaction path and the construction of C–C bonds could proceed efficiently on the BaO2 (110) facet. In this study, we developed a convenient and practical procedure to prepare BaO2 with preferential crystal facets, which could be used as a novel solid base catalyst for the sustainable upgrading of carbohydrate platforms.

Graphical abstract: Crystal facet-dependent upgrading of saccharides over barium peroxide to synthesize C-glycoside ketones

Supplementary files

Article information

Article type
Research Article
Submitted
23 Apr 2024
Accepted
28 Jun 2024
First published
02 Jul 2024

Inorg. Chem. Front., 2024,11, 5490-5498

Crystal facet-dependent upgrading of saccharides over barium peroxide to synthesize C-glycoside ketones

R. Lu, H. Chen, H. Yin, X. Zhang, S. Lv, X. Kong and F. Lu, Inorg. Chem. Front., 2024, 11, 5490 DOI: 10.1039/D4QI00992D

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