Unprotected Carbohydrate Conversion to Polyhydroxyalkyl Furans and Dihydrofurans: Improvement, Expansion, and Interruption of the Garcia Gonzalez Reaction via Homogeneous and Heterogeneous Catalysis
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Ronaghi, Nima
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Abstract
Biomass conversion of carbohydrates will lay the foundation for the future of materials, chemicals, and fuels. The Garcia Gonzalez reaction, an undervalued reaction coupling carbon nucleophiles with aldose sugars, can be an integral part of the carbohydrate conversion world, given the high yields, ease of tunability, mild conditions, and ease of setup. The improvement of the homogeneous catalysis of the Garcia Gonzalez reaction, using zirconium chloride as the catalyst, allows for more mild, facile synthesis of polyhydroxyalkyl and C-glycosyl furans. The expansion of the catalysts to a well-defined metal-organic framework, specifically UiO-66, showcases an example of heterogenizing a catalyst for a reaction system, as well as tuning the catalytic and morphological properties. Finally, interruption of the Garcia Gonzalez reaction is displayed by accessing a polyhydroxyalkyl dihydrofuran, rather than the polyhydroxyalkyl furans synthesized in the previous chapters, by using a cheap, recyclable magnesium oxide catalyst.
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2021-11-18
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Dissertation