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领先的催化方法之一，2010年诺贝尔化学奖因钯催化交叉偶联反应的发展而获得突出。我们最近开发了一种利用配体-底物非共价相互作用的方法，使携带远端卤化物的分子能够选择性交叉偶联。化学。Soc. 2018 doi: 10.1021/ jacks .8b08686)。这采用磺化布赫瓦尔德型配体，如sSPhos，这是市售的：磺酸基充当与底物的接触点。本项目将在其他具有区域选择性或对映体选择性的钯催化反应中更广泛地探索这一概念，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.