Arylation of hard heteroatomic nucleophiles using bromoarenes substrates and Cu, Ni, Pd-catalysts

摘要: Summary The arylation of different hard heteroatomic nucleophiles with arylbromides has been investigated using Pd, Ni or Cu-catalysts. reaction amines affords mostly the corresponding aromatic hydrocarbon by palladium catalysts, but expected substituted anilines are formed in good yields a nickel (II) catalyst. alcohols and copper presence base, comparatively regard to influence metals, ligands, primary secondary substituents on arylbromide. best conditions, bipyNiBr 2 KHCO 3 at 125°C, afford quantitative phenylalkyl ethers from alcohols. hydrolysis arylhalides into phenolate, actually hydroxide anion, also catalysts. As for alcohols, bromobenzene is much more reactive than chlorobenzene. needs an induction period which depends strongly temperature less significantly From results obtained radical scavengers reductors, new mechanism proposed arylhalides, including preliminary redox process leading (I) species then free catalytic cycle, oxidative addition reductive elimination processes. Last, catalyzed halogen exchange haloarenes, halide anions, investigated. equilibrated between phenyl bromide (60 %) phenyliodide (40 allows some co-catalysis system used as arylating agent 0.1 equivalent sodium iodide. All these transformations show that can exhibit diversified reactivity agents metallic