Preparation of Functionalized 2,7-Naphthyridines by Directed Lithiation with (2,2,6,6-Tetramethylpiperidyl)lithium and Their Regioselective Iron-Catalyzed Cross Couplings

Abstract

We report the regioselective functionalization of 2,7-naphthyridines by using (2,2,6,6-tetramethylpiperidyl)lithium as a base, together with the regioselective iron-catalyzed cross-coupling reactions of the products to give tetraalkylated 2,7-naphthyridines selectively.

Peri‐Functionalized Tetraazaperylenes: Strong Emitters for Molecular Polaritonics

“…To overcome this obstacle, the thiolato‐substituted compound 2 a was used as starting material for the preparation of 7 by the reaction of 2 a with the Gillmann cuprate LiCuMe 2 (Scheme 1 ). [43] This enabled a subsequent comparison of the material properties depending on the donor behavior of the peri substituent. Analogous to 3 , compound 7 was dechlorinated by a palladium catalyzed dehalogenation, thus again increasing the electron density in the aromatic core.…”

Preparation of Polyfunctional Naphthyridines by Cobalt-Catalyzed Cross-Couplings of Halogenated Naphthyridines with Magnesium and Zinc Organometallics

“…3 Although Fe-catalyzed cross-couplings have been used to functionalize chloronaphthyridines, the scope of such cross-couplings is quite limited. 4 Interestingly, Co-catalyzed cross-couplings generally display a broader reaction scope and have proved to be very useful for the functionalization of electron-deficient N-heterocycles. 5 We recently showed that the addition of appropriate ligands (e.g., sodium formate or pivalate) considerably extends the scope of these cross-couplings.…”