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Crystal facet-dependent upgrading of saccharides over barium peroxide to synthesize C-glycoside ketones
Inorganic Chemistry Frontiers ( IF 6.1 ) Pub Date : 2024-07-02 , DOI: 10.1039/d4qi00992d Rui Lu 1 , Hao Chen 1, 2 , Han Yin 1, 3 , Xi Zhang 1, 2 , Songqing Lv 1 , Xiangtao Kong 4 , Fang Lu 1
Inorganic Chemistry Frontiers ( IF 6.1 ) Pub Date : 2024-07-02 , DOI: 10.1039/d4qi00992d Rui Lu 1 , Hao Chen 1, 2 , Han Yin 1, 3 , Xi Zhang 1, 2 , Songqing Lv 1 , Xiangtao Kong 4 , Fang Lu 1
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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.
中文翻译：
通过过氧化钡对糖进行晶面依赖性升级以合成 C-糖苷酮
将丰富且易于获取的碳水化合物转化为高价值化学品是生物炼制领域的关键。然而，由于多功能基团的特殊性，未保护糖的选择性转化面临着巨大的挑战。在此，具有择优晶面的过氧化钡（BaO 2 ）在各种糖与乙酰丙酮的直接Knoevenagel缩合合成C-糖苷酮中表现出优异的性能。包括 XRD、TG-DSC、拉曼光谱、SEM 和 TEM 在内的表征方法表明，在空气气氛下煅烧的商业氧化钡（BaO）可以与氧气反应生成新物质 BaO 2 。此外，BaO 2 各晶面的相对比例可以通过调节焙烧条件来控制。此外，具有（110）晶面的BaO 2 表现出比具有主要（002）晶面的BaO 2 更好的反应性。结合实验研究和DFT计算的结果，发现不同晶面上基底的不同吸附能可以调节反应路径，并且C-C键的构建可以在BaO 2 ，其可用作碳水化合物平台可持续升级的新型固体碱催化剂。
更新日期：2024-07-02
中文翻译：
通过过氧化钡对糖进行晶面依赖性升级以合成 C-糖苷酮
将丰富且易于获取的碳水化合物转化为高价值化学品是生物炼制领域的关键。然而，由于多功能基团的特殊性，未保护糖的选择性转化面临着巨大的挑战。在此，具有择优晶面的过氧化钡（BaO 2 ）在各种糖与乙酰丙酮的直接Knoevenagel缩合合成C-糖苷酮中表现出优异的性能。包括 XRD、TG-DSC、拉曼光谱、SEM 和 TEM 在内的表征方法表明，在空气气氛下煅烧的商业氧化钡（BaO）可以与氧气反应生成新物质 BaO 2 。此外，BaO 2 各晶面的相对比例可以通过调节焙烧条件来控制。此外，具有（110）晶面的BaO 2 表现出比具有主要（002）晶面的BaO 2 更好的反应性。结合实验研究和DFT计算的结果，发现不同晶面上基底的不同吸附能可以调节反应路径，并且C-C键的构建可以在BaO 2 ，其可用作碳水化合物平台可持续升级的新型固体碱催化剂。
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