Catalytic Synthesis and Functionalisation of a Universal Aryl-Sulfur Intermediate

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The ability of chemists to produce specific organic molecules on demand, at low cost and on scales ranging from milligrams to multi-tonnes, has been central to many of the advances on which our quality of life now relies. The UK's fine chemical industry - particularly within the pharmaceutical and agrochemical sectors - continually faces new synthetic challenges, and is under increasing pressure to reduce the environmental impact of its operations. As such, there is constant demand for new synthetic methods that either provide more efficient access to known classes of compounds, or that open up previously unexplored areas of chemical space. Aryl-sulfur motifs feature in many societally-important molecules, including the sulfa drugs, anti-infectives that paved the way towards the modern healthcare we enjoy today. Formation of the C(aryl)-S linkage is often critical to the assembly of new aryl-sulfur-containing therapies, agrochemicals and materials, but - in many cases - is challenging to achieve in a mild and convenient fashion. Our research seeks to address these challenges through development of a robust and scalable method for C-S bond formation that avoids the malodorous, toxic and air sensitive intermediates that pervade organosulfur chemistry. The initial reaction products will then be exploited as a branching point from which to access all of the most important aryl-sulfur architectures, thereby demonstrating the ability of our methodology to deliver diverse, drug- and agrochemical-like scaffolds rapidly and under mild conditions. We will support this new methodology with detailed insight into how the system operates, and which variables are most critical for its successful application. Ultimately, this project will provide new tools to aid synthetic chemists in the preparation of a more diverse range of sulfur-containing molecules, in a more efficient manner. Given the contribution of pharmaceutical and agrochemical companies to the UK economy, this increased capability will be of benefit to UK plc. In addition, this project will provide a wealth of useful information and fundamental academic understanding that could guide the future development of new synthetic methods.