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Ni-Catalyzed Dimerization and Hydroperfluoroarylation of 1,3-Dienes.

Takanori IwasakiXin MinAsuka FukuokaLongzhi ZhuRenhua QiuTao YangMasahiro EharaArumugam SudalaiNobuaki Kambe
Published in: The Journal of organic chemistry (2018)
A nickel-catalyzed three-component coupling reaction between perfluoroarenes and two molecules of a 1,3-diene in the presence of an alkyl Grignard reagent, which acted as a hydride source, provided 3-perfluoroarylated-1,7-octadienes via 1,3-diene dimerization and subsequent perfluoroarylation upon C-F bond cleavage. The reaction proceeded smoothly in a regioselective manner by simply combining NiCl2 and PPh3 as a catalyst and tolerated various functional groups on the perfluoroarenes. When substituted perfluoroarenes were employed, the reaction selectively occurred at the para-position. Mechanistic studies revealed that an anionic Ni complex, generated upon the reaction of Ni(0) with two molecules of a 1,3-diene and an alkyl Grignard reagent, played an important role in the C-C bond forming step with perfluoroarenes. The C-F bond cleavage was found to be a relatively fast step in the catalytic cycle.
Keyphrases
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  • metal organic framework
  • dna binding
  • reduced graphene oxide
  • molecular docking
  • highly efficient
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  • molecular dynamics simulations