title: Palladium-catalyzed cascade C-H trifluoroethylation of aryl iodides and Heck reaction: efficient synthesis of ortho-trifluoroethylstyrenes.
abstract: A palladium-catalyzed selective C-H bond trifluoroethylation of aryl iodides has been explored. The reaction allows for the efficient synthesis of a variety of ortho-trifluoroethyl-substituted styrenes. Preliminary mechanistic studies indicate that the reaction might involve a key Pd(IV) intermediate, which is generated through the rate-determining oxidative addition of CF3CH2I to a palladacycle; the bulky nature of CF3CH2I influences the reactivity. Reductive elimination from the Pd(IV) complex then leads to the formation of the aryl-CH2CF3 bond.
authors: State Key Laboratory of Organometallic Chemistry, Shanghai, Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China).
authors: Hao
authors: H
authors: Zhang
authors: Pinhong
authors: P
authors: Chen
authors: Guosheng
authors: G
authors: Liu
mesh_terms: D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013343:Styrenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006845:Hydrocarbons, Fluorinated; D006847:Hydrocarbons, Iodinated; D009942:Organometallic Compounds; D013343:Styrenes; D010165:Palladium
keywords: CH activation; aryl iodides; fluorine; palladium; trifluoroethylation