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

Key words

atropisomeric axis - atropisomeric biaryls - C–H arylation

Publikationsverlauf

Eingereicht: 28. September 2020

Angenommen nach Revision: 22. Oktober 2020

Artikel online veröffentlicht:
24. November 2020

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