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

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.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01357416
Contributor : Laurent Jonchère <>
Submitted on : Monday, August 29, 2016 - 4:41:26 PM
Last modification on : Wednesday, October 21, 2020 - 3:13:52 AM

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Fatma Abdellaoui, Chiraz Youssef, Hamed Ben Ammar, Thierry Roisnel, Jean-François Soulé, et al.. Palladium-Catalyzed Regioselective C-H Bond Arylations of Benzoxazoles and Benzothiazoles at the C7 Position. ACS Catalysis, American Chemical Society, 2016, 6 (7), pp.4248--4252. ⟨10.1021/acscatal.6b00678⟩. ⟨hal-01357416⟩

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