51207-29-5Relevant academic research and scientific papers
Palladium-Catalyzed Zinc-Amide-Mediated C-H Arylation of Fluoroarenes and Heteroarenes with Aryl Sulfides
Otsuka, Shinya,Yorimitsu, Hideki,Osuka, Atsuhiro
supporting information, p. 14703 - 14707 (2015/10/20)
C-H arylation of polyfluoroarenes and heteroarenes with aryl sulfides proceeds smoothly with the aid of a palladium-N-heterocyclic carbene catalyst. A bulky zinc amide, TMPZnCl an effective base to generate the corresponding arylzinc species in situ. This arylation protocol is practically much easier to perform than our previous method, which necessitates preparation of the arylzinc reagents in advance from the corresponding aryl halides. Aryl sulfides that are prepared through sulfur-specific reactions, such as SNAr sulfanylation and extended Pummerer reactions, undergo this direct arylation, offering interesting transformations that are otherwise difficult to achieve with conventional halogen-based organic synthesis.
Synthesis and structural characterization of the first unsymmetrical diarylpalladium complex trans-Pd(C6F5)(2,4,6-C 6F3H2)(PEt3)2, derived from transmetallation between 2,4,6-tri
Nishihara, Yasushi,Onodera, Hiroyuki,Osakada, Kohtaro
, p. 192 - 193 (2007/10/03)
The reactions of 2,4,6-trifluorophenylboronic acid with aryl(iodo)palladium(II) complexes, trans-Pd(C6F5)I(PR 3)2 (PR3 = PEt3, PMe2Ph, PMePh2) in the presence of Agsu
Fluorinated biphenyls from aromatic arylations with pentafluorobenzenediazonium and related cations. Competition between arylation and azo coupling
Kosynkin, Dmitry,Bockman, T. Michael,Kochi, Jay K.
, p. 2003 - 2012 (2007/10/03)
High yields of the mixed perfluorinated biaryls (C6F5-Ar) are obtained by the catalytic dediazonlatlon of the pentafluorobenzenediazonium salt (C6F5N2+BF4-) in acetonitrile solutions containing various aromatic substrates (ArH) together with small amounts of iodide salts. Activated (electron-rich) as well as deactivated (electron-poor) arenes are successfully pentafluorophenylated by this method. The arylation is distinct from the azo coupling of the same substrates, which takes place in the absence of the iodide catalyst and yields the corresponding diazene (C6F5N=N-Ar) as product. The catalytic role of iodide, and the isomeric product distributions obtained with this procedure indicate that the arylation proceeds via the pentafluorophenyl radical in a efficient homolytic chain process. Since azo coupling involves electrophilic aromatic substitution of electron-rich ArH by C6F5N2+, the two competing pathways are distinct and do not have reactive intermediates in common.
