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Keywords:

  • carbanions;
  • C[BOND]N coupling;
  • dianions;
  • nitrogen heterocycles;
  • oxidative coupling
Thumbnail image of graphical abstract

What a couple! An intramolecular, C(sp3)[BOND]N coupling to afford azacycles is reported. This reaction proceeds through the oxidation of benzylic C,N-dianions with iodine and builds on an earlier discovery during the synthesis of the natural product lyconadin A. The current study employs conformationally unbiased substrates with less acidic C[BOND]H bonds and less reactive nitrogen nucleophiles. ZnCl2 was identified as an important additive.