Palladium-Catalyzed Asymmetric Synthesis of Silicon-Stereogenic Dibenzosiloles via Enantioselective C–H Bond Functionalization

• Published in: Journal of the American Chemical Society Vol. 134; no. 17; pp. 7305 - 7308
• Main Authors: Shintani, Ryo, Otomo, Haruka, Ota, Kensuke, Hayashi, Tamio
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 02.05.2012; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; HYDROGENATION REACTIONS; LIGHT-EMITTING POLYMERS; DIRECT ARYLATION; INTRAMOLECULAR ARYLATION; 1,4-PALLADIUM MIGRATION; POLYCYCLIC AROMATIC-HYDROCARBONS; METALATION-DEPROTONATION MECHANISM; PHOTOPHYSICAL PROPERTIES; C2-SYMMETRICAL BIS(PHOSPHOLANES); PROTON-ABSTRACTION MECHANISM

A Pd-catalyzed asymmetric synthesis of Si-stereogenic dibenzosiloles is developed through enantioselective C–H bond functionalization of prochiral 2-(arylsilyl)aryl triflates. High chemo- and enantioselectivities are achieved by employing a Josiphos-type ligand under mild conditions.