Challenging Atroposelective C-H Arylation

Abstract

Atropisomeric molecules are privileged scaffolds, not only as ligands for asymmetric synthesis, but also as biologically active products and advanced materials. Although very attractive from a sustainability viewpoint, the direct construction of the stereogenic axis through asymmetric C-H arylation is very challenging and consequently only a few examples have been reported. This short review summarizes these very recent results on the atropo-enantio or diastereo­selective synthesis of atropisomeric (hetero)biaryl molecules; transformations during which the Ar-Ar atropisomeric axis is formed during the C-H activation process. 1 Introduction 2 Atropo-enantioselective Intermolecular Pd-Catalyzed C-H Arylation of Thiophene Derivatives 3 Atropodiastereoselective Intermolecular Pd-Catalyzed C-H Arylation towards Terphenyl Scaffolds Bearing Two Atropisomeric Axes 4 Atropo-enantioselective Intramolecular Pd-Catalyzed C-H Arylation towards Atropisomeric Benzodiazepinones 5 Atropo-enantioselective Intermolecular Pd-Catalyzed C-H Arylation of Heteroarenes 6 Rh-Catalyzed Atropo-enantioselective C-H Arylation of Diazonaphthoquinones 7 Conclusion.