Unfunctionalised Arenes in Cross-Coupling Processes

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Carbon-hydrogen bonds are the most common bonds found in organic molecules. In this proposal we describe an investigation to develop methods that allows these bonds to be used as handles for the formation of useful carbon-carbon bonds.The proposed research is concerned with developing palladium catalysed coupling reactons between vinyl triflates (or halides) and simple aryl C-H systems. The ability to use aryl C-H systems as one of the components in a coupling reaction offers significant advantages over exisiting methods; paramount amongst these are the ease of synthesis of the required coupling partners and the significant reduction in the amount of waste byproducts generated. The project will focus on intramolecular couplings, i.e., cyclisation reactions.The initial phase of the project will define efficient catalyst systems using parallel screening methods. These model systems will also be used to probe the effects of different electronic and streric substituents on the efficiency of the cyclisations. The second phase of the project is to explore the scope of the developed chemistry. Initially carbocyclic systems will be studied before moving on to evaluate the synthesis of heterocyclic systems. The final phase of the project will attempt to combine the developed cyclisation chemistry with exisiting palladium catalysed reactions to develop new reaction cascades. These domino sequences will use simple readily available starting materials to produce complex systems in one-pot reactions.