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

在过去的50年里，钯催化已经成为有机合成中的主要催化方法之一，2010年诺贝尔化学奖的颁发突出了对钯催化交叉偶联反应的发展。我们最近开发了一种使用配体-底物非共价相互作用的方法，使含有远程卤化物的分子能够进行位置选择性交叉偶联(J.Am化学。SoC。2018年DOI：10.1021/Jacs.8b08686)。这使用了磺化的Buchwald类型的配体，如sSPhos，这是可以商业获得的：磺酸基充当与底物的接触点。这个项目将在各种其他钯催化的反应中更广泛地探索这一概念，这些反应具有区域选择性或对映体选择性，并证明非共价催化可以作为解决合成化学中一些突出挑战的一般方法。

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.