3 years ago

Convenient Access to meta-Substituted Phenols by Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling and Oxidation

Convenient Access to meta-Substituted Phenols by Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling and Oxidation
Zi Wang, Arturo Orellana
We report a new approach to the synthesis of meta-substituted phenols in which a single palladium catalyst accomplishes a Suzuki–Miyaura cross-coupling between a β-chlorocyclohexenone and an arylboronic acid, and oxidation of the resulting cyclohexenone to the corresponding phenol upon introduction of a terminal oxidant and electron transfer mediator. Notably, this method also allows ready access to ortho, meta-disubstituted phenols, sterically congested biaryl phenols, and more highly substituted phenols. Catalytic two-step: The tandem palladium-catalyzed cross-coupling of b-chlorocyclohexenones and subsequent palladium-catalyzed oxidation provide access to meta-substituted and ortho,meta-disubstituted phenols.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702651

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