Abstract
Highly π-extended hetero-cyclic/aromatic skeletons are of great importance as they can be utilized in many organic material based technologies. Therefore, developing efficient, pre-activation-free, synthetic procedures for the rapid build-up of these complex structures remains a high priority objective. The herein presented approach delivers highly fused carbazole skeletons from simple naphthylamine derivatives.
Highlights
P-extended hetero-cyclic/aromatic skeletons are of great importance as they can be utilized in many organic material based technologies
The cost associated to the stoichiometric excess of the precious 2,20-diiodobiphenyl substrate (IV) or any other desired diiodo backbone, significantly limits the applicability and price of the final carbazole based target material
We inspired ourselves from the historical reports describing the more challenging direct oxidation of N-phenyl-2-naphthylamine, wherein the yield of corresponding annulated carbazole 2b does not exceed 25%
Summary
The presented approach delivers highly fused carbazole skeletons from simple naphthylamine derivatives. In a recent and inspiring work from Ito & Itami, a highly annulated carbazole structure (2a, Scheme 1) could be accessed from a simple pyrrole (IV) and a (not so trivial) 2,20-diiodobiphenyl structure (V).[3] This previous synthetic method operates through a tetrafold palladium catalyzed Mizoroki–Heck-like reaction.[3] The cost associated to the stoichiometric excess of the precious 2,20-diiodobiphenyl substrate (IV) or any other desired diiodo backbone, significantly limits the applicability and price of the final carbazole based target material.
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