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Development of Solvent-Free Catalyzed Organic Reaction under Mechanochemical Conditions
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Development of Solvent-Free Catalyzed Organic Reaction under Mechanochemical Conditions
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Development of Solvent-Free Catalyzed Organic Reaction under Mechanochemical Conditions
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Dissertation
Development of Solvent-Free Catalyzed Organic Reaction under Mechanochemical Conditions
2016
Overview
Chemical waste has become a major problem for the chemical industry. For centuries, scientists desperately sought ways to reduce chemical waste including developing new methods and materials, especially in the field of synthetic organic chemistry due to the massive amount of solvent waste generated during the reaction process. The Mack group successfully utilized high speed ball milling (HSBM), a solvent-free mechanochemical technique to facilitate and conduct chemical reactions. In ball milling, the ball bearings grind reactants to small size of particles, mixing them in a reaction vial, and during the fierce shaken process, the ball hits the wall and provides energy for reactants to overcome the energy barrier to form products. After two decades of development, more and more studies and research revealed this new world and now ball milling has been recognized as a potential sustainable method for conducting various organic reactions. In this dissertation, I have developed sustainable catalysis for coupling reactions and cycloaddition reactions under mechanochemical conditions. In the first chapter, I introduce the concept of green chemistry and mechanochemistry, elaborate on the solvent selection problem and ball milling applications in recent organic chemistry. In chapter 2 and chapter 3, I will discuss the details about using simple catalyst and polymer supported catalyst to perform dimerization of terminal alkynes in a ball mill, which was not only a sustainable method to form products but also enable to tune either product. The new solvent-free surface catalysis for cycloaddition reactions will discuss in chapter 4 and chapter 5, there I will introduce a novel approach by using metal foil as a cheap, recyclable catalyst to catalyze cyclopropanation and cyclopropenation through reactive carbenoid reagent. The last chapter will introduce a versatile approach for X-H insertion reactions catalyzed by cooper surface via ball milling.
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