Harnessing Sulfur Dioxide for Catalysis

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Sulfonyl units, that is the -SO2- arrangement of atoms, are functional groups that feature in a significant number of pharmaceuticals, argochemcials and materials. Conventional syntheses of these types of molecules usually involve two or three synthetic operations, and often feature low-yielding steps. The chemistry involved also limits the substrates that can be converted to sulfonyl-containing molecules. This proposal seeks to develop an alternative synthesis of this class of molecules; the proposed synthesis will be achieved in a single operation, employ readily available reagents and substrates, and be conducted under mild conditions. The key to the proposed synthesis is to employ a three-component synthesis involving the catalytic combination of an aryl halide, an nucleophile and sulfur dioxide. Achieving the synthesis in a single operation will have significant advantages in terms of waste production, energy required, as well as the time needed to prepare the desired compounds. These are important considerations for both small scale discovery synthesis, as well as the large scale synthesis of these materials. The developed methodology should also be applicable to the preparation of related molecules derived from alternative starting materials such as non-functionalised arenes or alkene and alkynes. The project will explore the application of the developed method to the synthesis or selected target structures that are difficult to access using conventional methods, and to the synthesis of heterocycles. Application of the developed catalytic methods to the synthesis of new materials, using polymerisation chemistry, will also be preliminarily investigated.