Directed Palladium(II)-Catalyzed Intermolecular Anti-Markovnikov Hydroarylation of Unactivated Alkenes with (Hetero)arylsilanes

Org Lett. 2020 Nov 20;22(22):9022-9028. doi: 10.1021/acs.orglett.0c03416. Epub 2020 Nov 5.

Abstract

We describe herein a regioselective palladium(II)-catalyzed intermolecular hydroarylation of unactivated aliphatic alkenes with electronically and sterically diverse (hetero)arylsilanes under redox-neutral conditions. A removable bidentate 8-aminoquinoline auxiliary was readily employed to dictate the regioselectivity, prevent β-hydride elimination, and facilitate protodepalladation. This silicon-based protocol features a broad substrate scope with excellent functional group compatibility and enables an expeditious route to a variety of γ-aryl butyric acid derivatives in good yields with exclusive anti-Markovnikov selectivity.