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Keywords:

  • C[BOND]F bond activation;
  • cobalt;
  • imine;
  • organozinc reagent;
  • C,C-coupling

Abstract

In this paper the C[BOND]F bond activation of polyfluoroaryl imines is explored at cobalt(0) center with an imine-N atom as an anchoring group. The reaction of F5C6-CH[DOUBLE BOND]N-(2′-ClC6H4) (2) and F5C6-CH[DOUBLE BOND]N-C6H5 (3) with Co(PMe3)4 afforded the C[BOND]F bond activation products (ortho-F4C6-CH[DOUBLE BOND]N-(2′-ClC6H4))Co(I)(PMe3)3 (5) and (ortho-F4C6-CH[DOUBLE BOND]N-C6H5)Co(II)(F)(PMe3)2 (6), while only π-(C[DOUBLE BOND]N) coordinated cobalt(0) complex (2,4,5-F3C6H2-CH[DOUBLE BOND]N-(4′-ClC6H4))Co(0)(PMe3)3 (4) was obtained from 2,4,5-F3C6H2-CH[DOUBLE BOND]N-(4′-ClC6H4) (1) without C[BOND]F bond activation. Complexes 46 were characterized through X-ray single crystal diffraction. It was also found that dialkylation of N-(perfluorobenzylidene)benzenamine with organozinc reagents could be catalyzed by Co(PMe3)4 via C,C-coupling reaction under mild conditions.