Development of Visible Light Photoredox Catalyzed Reactions Using Organo-silane Reagents.

Abstract

This thesis describes the research conducted on the ‘Development of the Visible Light Photoredox Catalyzed Reactions Using Organo-silane reagents. Photoredox catalysis made it possible to generate the radical in more environmentally friendly, cost-effective, and mild methods. It is revolutionizing and changing the paradigm of traditional radical reactions. Given silicon's abundance, non-hazardous nature, and radical stabilization tendency, it is advantageous to use silicon reagents for radical reactions by photoredox catalysis. Silicon-containing organic reagents are prepared and used for the generation of the stabilized radicals, and their reaction with the several radical coupling reagents, to develop the novel photochemical reactions. Chapter 1 provides a succinct guide to photoredox catalysis, types of photoredox cycles, and its role in eco-friendly radical reactions. It also gives a brief overview of the silicon reagent, its abundance and stabilization, role in the generation of radicals, and photochemical methods based on organo-silicon reactions. Following an outline of Photoredox catalysis and organo-silicon reagents, Chapter 2 demonstrates allyl silicon reagents as an allyl radical precursor that undergoes addition to electron-deficient olefins to produce regioselective allylation products in high yields. It also provides evidence of synthetic utility, mechanism. In Chapter 3, allyl silane is used to allylate the essential synthesis intermediates, α-halo carbonyl compounds. It also illustrates the mechanism and mechanistic experiments to demonstrate the reaction mechanism. In Chapter 4, alokoxymethyl silane is used as an alkoxy radical precursor, and the coupling reaction with the imine to produce β-amino ether is described. It also showed oxidation deprotection of the β amino ether in a one-pot sequential process to prepare the vicinal amino alcohol. The tolerance of reactions to the labile functional group is shown using multiple photosensitive functional groups. Furthermore, the significance of this reaction is shown by translating it on a preparative scale, conducting it in sunlight and transforming the materials into a variety of synthetically useful substrates.