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Convenient Access to meta ‐Substituted Phenols by Palladium‐Catalyzed Suzuki–Miyaura Cross‐Coupling and Oxidation
Author(s) -
Wang Zi,
Orellana Arturo
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702651
Subject(s) - phenols , palladium , phenol , catalysis , chemistry , steric effects , combinatorial chemistry , organic chemistry , coupling (piping) , materials science , metallurgy
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.