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Palladium-Catalyzed Aerobic Dehydrogenation of Substituted Cyclohexanones to Phenols
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Palladium-Catalyzed Aerobic Dehydrogenation of Substituted Cyclohexanones to Phenols
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Journal Article
Palladium-Catalyzed Aerobic Dehydrogenation of Substituted Cyclohexanones to Phenols
2011
Overview
Aromatic molecules are key constituents of many pharmaceuticals, electronic materials, and commodity plastics. The utility of these molecules directly reflects the identity and pattern of substituents on the aromatic ring. Here, we report a palladium(II) catalyst system, incorporating an unconventional ortho-dimethylaminopyridine ligand, for the conversion of substituted cyclohexanones to the corresponding phenols. The reaction proceeds via successive dehydrogenation of two saturated carbon-carbon bonds of the six-membered ring and uses molecular oxygen as the hydrogen acceptor. This reactivity demonstrates a versatile and efficient strategy for the synthesis of substituted aromatic molecules with fundamentally different selectivity constraints from the numerous known synthetic methods that rely on substitution of a preexisting aromatic ring.
Publisher
American Association for the Advancement of Science,The American Association for the Advancement of Science
Subject
/ Alicyclic compounds, terpenoids, prostaglandins, steroids
/ Catalysts: preparations and properties
/ drugs
/ Exact sciences and technology
/ General and physical chemistry
/ hydrogen
/ Ketones
/ Kinetics
/ Ligands
/ Noncondensed benzenic compounds
/ oxygen
/ Phenols
/ Phenols - chemical synthesis
/ plastics
/ Reagents
/ Strategy
