Micellar catalysis enabling sustainable synthesis
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The concept of micellar catalysis (Chemistry in water) and its applications in the development of various sustainable methodologies are discussed in this dissertation. It also discusses the synthesis of rationally designed amphiphiles and their multiple functions for sustainable synthesis. These novel methodologies reduce the reliance on expensive ligands and toxic organic solvents compared to traditional methods. Sustainable methodologies for the synthesis of valuable organic compounds, such as unsymmetrical biaryl ketones, and functionalized indoles, have been developed. In addition to this, a methodology for the functionalization of styrenes has been developed under aqueous conditions. Chapter 1 reviews the concept of Micellar catalysis (a reaction in water) and analytical techniques for probing the mechanism of reactions in a micellar environment. Chapter 2 discusses the development of a ligand-free protocol for the synthesis of asymmetrical biaryl ketones. The current methodologies suffer from the use of expensive multistep synthesized ligands and toxic organic solvents. With the developed methodology, biaryl ketones were developed without the use of ligands in aqueous conditions. Moreover, the new methodology is easy to execute. Chapter 3 highlights the synthesis of a novel surfactant for ligand-free gold-catalyzed synthesis of functionalized indoles. The methodology is easy to execute and does not require the use of toxic organic solvents. A wide variety of functionalized indoles were obtained, including the complex molecules from the Merck informer library. Chapter 4 discusses the sustainable protocol for the functionalization of styrenes with azides and carboxylic acids under aqueous micellar conditions using our rationally designed PS-750-M as an amphiphile. Under the shielding effect of micelles, styrenes, and azides can be used safely, even if they proceed through radical formation.
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Ph. D.