Dehydroaronatization of Quionoxalines: One-Step Syntheses of Trinuclear 1,6,7,12,13,18-Hexaazatrinaphthylene Titanium Complexes

Ingmar M. Piglosiewicz, Rüdiger Beckhaus, Wolfang Saak, and Detlev Haase
J. Am. Chem. Soc. 2005, 127 14190 - 14191.


We report the spontaneous coupling of N-heterocycles, initiated by C-H bond activation reactions. The reaction of quinoxalines and the titanocene acetylene complex Cp2Ti{ η2 -C2(SiMe3)2}, as an excellent titanocene source, results in the formation of trinuclear 1,6,7,12,13,18-hexaazatrinaphthylene (HATN) titanium complexes. These HATN titanium complexes are thermally stable but sensitive to air and moisture. A three-fold dehydrogenative C-C coupling is proposed as the main step in the presented synthetic procedure. Particularly using commercial starting materials, an efficient route for the dehydrogenative coupling of N-heterocycles, leading to multidentate ligands, has been established.

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