Palladium-Catalyzed Regioselective C-H Bond Arylations of Benzoxazoles and Benzothiazoles at the C7 Position

Fatma Abdellaoui; Chiraz Youssef; Hamed Ben Ammar; Thierry Roisnel; Jean-François Soulé; Henri Doucet

doi:10.1021/acscatal.6b00678

Journal articles

Palladium-Catalyzed Regioselective C-H Bond Arylations of Benzoxazoles and Benzothiazoles at the C7 Position

Fatma Abdellaoui ^{1, 2, 3, 4} Chiraz Youssef ^{4, 3} Hamed Ben Ammar ^{4, 3} Thierry Roisnel ² Jean-François Soulé ² Henri Doucet ²

1 UM - Université de Monastir - University of Monastir

2 ISCR - Institut des Sciences Chimiques de Rennes

3 FSM - Faculté des Sciences de Monastir

4 Laboratoire de Synthèse Organique Asymétrique et Catalyse Homogène

Abstract : We report herein, a very simple catalytic system for the direct arylation of benzoxazole and benzothiazole derivatives at C7 position, namely, phosphine-free PdCl2 associated with PivOK in NMP at 150 degrees C. (Thio)phenoxy chelation-assisted Pd-catalyzed C-H bond cleavage, from an opened intermediate, was proposed to explain this unique regioselectivity. This reaction allows the synthesis of 2-amino-6-arylphenols through the ring opening of the benzoxazole.

Keywords : including free (nh)-imidazole direct c-2 arylation aryl bromides coupling reactions halides derivatives azoles functionalization heterocycles phenols

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Journal articles

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Chemical Sciences

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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01357416
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Submitted on : Monday, August 29, 2016 - 4:41:26 PM
Last modification on : Wednesday, April 7, 2021 - 3:18:08 PM

Palladium-Catalyzed Regioselective C-H Bond Arylations of Benzoxazoles and Benzothiazoles at the C7 Position

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Palladium-Catalyzed Regioselective C-H Bond Arylations of Benzoxazoles and Benzothiazoles at the C7 Position

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