Enantioselective Palladium-Catalyzed Suzuki–Miyaura Reactions Enabled by Ionic Ligand–Substrate Interactions

Abstract

Enzymes harness an array of noncovalent interactions to accomplish stereospecific transformations. Similarly, chemists have engineered chiral catalysts capable of eliciting noncovalent interactions for asymmetric synthesis. In this context, incorporating ionic groups into synthetic transition-metal catalysts represents a promising design element for enantioselective reactions by engaging electrostatic interactions between ligands and substrates. However, the nondirectional nature of ionic interactions presents a unique challenge in precise transmission of chirality. This account summarizes our recent work on developing phosphine ligands possessing nonligating ionic groups for exerting long-range stereocontrol in Suzuki–Miyaura reactions.

1 Introduction

2 Remote Quaternary Stereocenters

3 Mechanically Planar Chiral Rotaxanes

4 Atropo-enantioenriched Biaryls

5 Conclusions

Key words

stereoselectivity - cross-coupling - noncovalent interactions - quaternary stereocenters - rotaxanes - atropisomerism - mechanically planar chirality - ionic interactions

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