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Issue 8, 2020
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Palladium-catalyzed aerobic synthesis of ortho-substituted phenols from cyclohexanones and primary alcohols

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Abstract

Due to the importance of phenols as structural cores and precursors of chemical products, synthesis of site-specific substituted phenols is highly desirable and a significant challenge. An aerobic palladium-catalyzed site-specific synthesis of ortho-substituted phenols from cyclohexanones and primary alcohols via an oxidation/aldol/dehydration/aromatization process has been developed. Various substituted cyclohexanones and primary alcohols are successfully transformed into ortho-substituted phenols. In addition, this catalytic reaction uses air as the terminal oxidant and generates water as the sole by-product. Furthermore, the method can also be extended to polyhydroxyl substituted substrates with high chemoselectivity between primary and secondary alcohols. This method provides a greener tool for synthesizing primary alkyl ortho-substituted phenols.

Graphical abstract: Palladium-catalyzed aerobic synthesis of ortho-substituted phenols from cyclohexanones and primary alcohols

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Supplementary files

Article information


Submitted
02 Dec 2019
Accepted
16 Dec 2019
First published
03 Jan 2020

Chem. Commun., 2020,56, 1239-1242
Article type
Communication

Palladium-catalyzed aerobic synthesis of ortho-substituted phenols from cyclohexanones and primary alcohols

H. Zeng, J. Yu and C. Li, Chem. Commun., 2020, 56, 1239 DOI: 10.1039/C9CC09347H

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