title: Palladium-catalyzed intramolecular C-H difluoroalkylation: synthesis of substituted 3,3-difluoro-2-oxindoles.
abstract: The synthesis of 3,3-difluoro-2-oxindoles through a robust and efficient palladium-catalyzed CH difluoroalkylation is described. This process generates a broad range of difluorooxindoles from readily prepared starting materials. The use of BrettPhos as the ligand was crucial for high efficiency. Preliminary mechanistic studies suggest that oxidative addition is the rate-determining step for this process.
authors.affiliation: Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA).
authors.forename: Shi-Liang
authors.initials: SL
authors.lastname: Shi
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D000478:Alkylation; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D000078183:Oxindoles; D010165:Palladium / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D005461:Fluorine; D010165:Palladium; D002244:Carbon; D006859:Hydrogen
keywords: CH activation; cross-coupling; fluorine; heterocycles; palladium