Mono or double Pd-catalyzed C – H bond functionalization for the annulative π -extension of 1,8-dibromonaphthalene: a one pot access to fluoranthene derivatives

Abstract
The Pd-catalyzed annulative π-extension of 1,8-dibromonaphthalene for the preparation of fluoranthenes in a single operation has been investigated. With specific arenes such as fluorobenzenes, the Pd-catalyzed double functionalization of C–H bonds yields the desired fluoranthenes. The reaction proceeds via a palladium-catalyzed direct intermolecular arylation, followed by a direct intramolecular arylation step. As the C–H bond activation of several benzene derivatives remains very challenging, the preparation of fluoranthenes from 1,8-dibromonaphthalene via Suzuki coupling followed by intramolecular C–H activation has also been investigated to provide a complementary method. Using the most appropriate synthetic route and substrates, it is possible to introduce the desired functional groups at positions 7–10 on fluoranthenes.

Beilstein J. Org. Chem. 2024, 20, 427–435. doi:10.3762/bjoc.20.37

Source: Beilstein Journal of Organic Chemistry - February 23, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: catalysis – H bond functionalization direct arylation fluoranthenes palladium Full Research Paper Source Type: research