Using Non-Covalent Catalysis to Influence Regioselectivity and Enantioselectivity in Organic Synthesis

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Palladium catalysis has become established over the last 50 years as one of the leading catalytic methods in organic synthesis, highlighted by the award of the 2010 Nobel Prize for Chemistry for the development of palladium-catalysed cross-coupling reactions. We have recently developed a method using ligand-substrate non-covalent interactions that enables site-selective cross-coupling of molecules bearing remote halides (J. Am. Chem. Soc. 2018 doi: 10.1021/jacs.8b08686). This employed sulfonylated Buchwald-type ligands such as sSPhos, which is commercially available: the sulfonate group acted as the point of contact with the substrate. This project will explore this concept more widely in a variety of other palladium-catalysed reactions that feature regioselectivity or enantioselectivity choices and demonstrate that non-covalent catalysis can used as a general approach in tackling some of these outstanding challenges in synthetic chemistry.