Intermolecular Followed by Intramolecular Palladium-Catalyzed Direct Arylation for the Synthesis of pi-Extended Aromatic Compounds Containing One or Two Heteroelements

Abstract : Herein, we report that palladium-catalyzed C-H bond activation can overcome some of the challenges in the preparation of pi-extended aromatics containing one or two heteroelements, which are important structures in organic materials science. The sequential palladium-catalyzed intermolecular direct C5-arylation of heteroarenes by aryl bromides, followed by bromination of the heteroarene unit with N-bromosuccinimide, and finally palladium-catalyzed intramolecular direct arylation allowed the synthesis of the desired phenanthro[9,10-b]thiophenes, phenanthro[9,10-b]furans, phenanthro[9,10-b]thiazoles, acenaphtho[1,2-d]thiophenes, and acenaphtho[1,2-d]thiazoles in only three steps.
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Submitted on : Wednesday, September 4, 2019 - 1:18:23 PM
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Bilel Bouzayani, Ridha Ben Salem, Jean-François Soulé, Henri Doucet. Intermolecular Followed by Intramolecular Palladium-Catalyzed Direct Arylation for the Synthesis of pi-Extended Aromatic Compounds Containing One or Two Heteroelements. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2019, pp.4581-4588. ⟨10.1002/ejoc.201900775⟩. ⟨hal-02278417⟩

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