A one-step copper-catalyzed
reaction of aldehyde-derived N-substituted
hydrazones with CCl4 resulted in efficient synthesis of
4,4-dichloro-1,2-diazabuta-1,3-dienes. It was proven that this C–C
bond-forming cascade reaction operates via an addition of trichloromethyl
radical to the CN bond of hydrazone followed by a base-induced
elimination of HCl. The reaction was found to be very general, as
diverse hydrazones possessing various aromatic groups at N-site, as
well as aromatic, aliphatic, and heterocyclic substituents at C-site,
are capable partners for coupling with a wide range of polyhalogenated
compounds (CCl3Br, CBr4, CCl3CN,
CCl3COOEt, CCl3CF3, CBr3CF3) to produce a family of functionalized 1,2-diazabuta-1,3-dienes.
It was demonstrated that the prepared heterodienes are highly versatile
building blocks for straightforward assembly of various valuable acyclic
and heterocyclic molecules.