DEVELOPMENT OF GREEN PROTOCOLS FOR INDIUM-MEDIATED ALLYLATION REACTIONS

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2024-07-21

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North Dakota State University

Abstract

Green chemistry, a developing topic within chemistry that impacts all its branches and applications, has become a prominent focus in many research labs. The primary emphasis of our laboratory is on the advancement of eco-friendly methods for synthesizing and modifying small molecules. In order to accomplish this goal, we utilized safer substances, such as indium, to construct C-C using many techniques, including stoichiometric, catalytic, enantiopure, and racemic procedures. The thesis, titled ”Development of Green Protocols for Indium-Mediated Reactions,” is structured into four extensive chapters. Chapter one presents a comprehensive introduction to important concepts including the fundamental principles of green chemistry, the distinctive properties of allylindium species, the significance of indium in advancing green chemistry, and the application of solid-supported materials in organic synthesis. In chapter two, we investigate in the nature of allylindium species formed in-situ. To achieve this, we analyze mass spectrometery chromatograms in different conditions related to our reactions. We also utilized real-time NMR to investigate the relationship between species formed in terms of equilibrium and most-yielding species. Finally, we assigned the species formed in-situ based on our observations regarding the spectroscopic utilized. Chapter three delves into the pivotal significance of amino acids in our investigation of the indium-mediated allylation of isatin. We performed a systematic investigation of amino acids and related substances, along with continuous monitoring of the reactive allylindium species during the reaction. This investigation has revealed the essential characteristics that additives must possess in order to properly aid the reaction. In chapter four we describe our endeavors to create a system that allows for the recycling of indium and amino acid additives in the process of allylation of isatin. In this experiment, amino acids were loaded on activated silica gel along with indium weight percentages. This system was evaluated in its ability to be recycled for many reaction cycles. In addition, we assessed the efficacy of imidazole-based templates in ketone allylation. We also presented a method where we incorporate the amino acid additive into the isatin substrate, which is a huge step towards atom economy and practicality.

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INDIUM, ALLYLATION, ISATIN, GREEN CHEMISTRY, AMINO ACIDS

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