Abstract
ABSTRACT Arynes are a truly amazing species which has found wide applications in organic chemistry despite the fact that it has to be generated in situ. Particularly, the introduction of 2-(trimethylsilyl)phenyl triflate as an aryne precursor that operates under mild reaction conditions has enabled the development of a variety of reactions which also includes transition-metal mediated aryne carbon-carbon bond forming processes. This thesis describes five new reactions that focus on the application of arynes in organic synthesis employing o-silyl aryltriflates as aryne precursors. The first three chapters describes palladium-catalyzed carbopalladation reactions involving arynes with each chapter dealing with a facet of palladium chemistry viz., [2 + 2 + 2] cyclotrimerization, three-component coupling and C-H activation. The fourth chapter involves a novel nickel-catalyzed coupling involving arynes. The final chapter deals with the ene reaction of arynes with alkynes. □Chapter 1 is devoted to give a small introduction as well as a brief review of aryne chemistry over the past 100 years. However, the second half of the chapter 1 reviews almost all the reports that have appeared involving o-silyl aryltriflates as aryne precursors. □Chapter 2 describes a [2+2+2] cocyclotrimerization of arynes with bicyclic alkenes leading to polyaromatic hydrocarbons. Chapter 3 deals about a palladium-catalyzed three-component coupling of arynes, allylhalides and arylorganometallic reagents. Chapter 4 illustrates a palladium-catalyzed annulation reaction of arynes with aryl halides leading to functionalized triphenylenes. Chapter 5 explains a nickel-catalyzed three-component coupling involving arynes, enones and organoboronic acids. Chapter 6 is about the ene reaction of arynes with alkynes.