Directed Palladium(II)-Catalyzed Intermolecular Anti-Markovnikov Hydroarylation of Unactivated Alkenes with (Hetero)arylsilanes
Mingzhu Lu, Haiqing Luo, Zhengsong Hu, Changdong Shao, Yu‐He Kan, Teck‐Peng Loh
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.
Topics & Concepts
ChemistryMarkovnikov's ruleRegioselectivityCatalysisPalladiumIntermolecular forceArylCombinatorial chemistrySteric effectsDenticityFunctional groupSelectivityOrganic chemistryMoleculeAlkylMetalPolymerCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSulfur-Based Synthesis Techniques