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

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2024 Feb 27

PMID 38410779

Authors

Nahed Ketata

Linhao Liu

Ridha Ben Salem

Henri Doucet

Affiliations

Soon will be listed here.

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.

Citing Articles

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[]fluoranthenes via a Pd-catalyzed Suzuki-Miyaura/C-H arylation cascade.

Yence M, Ahmadli D, Surmeli D, Karacaoglu U, Pal S, Turkmen Y Beilstein J Org Chem. 2025; 20:3290-3298.

PMID: 39749309 PMC: 11693970. DOI: 10.3762/bjoc.20.273.

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