Anodic Oxidation: An Attractive Alternative to CAN‐Mediated Cleavage of para‐Methoxyphenyl Ethers

para‐Methoxyphenyl (PMP) ether is a very convenient protecting group for the alcohol function; however, its cleavage requires strong oxidative conditions. In this field, the use of powerful ceric ammonium nitrate has been widely described, despite the fact that its strong nature results in the forma...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2009-07, Vol.2009 (19), p.3138-3140
Main Authors: Vaxelaire, Carine, Souquet, Florence, Lannou, Marie‐Isabelle, Ardisson, Janick, Royer, Jacques
Format: Article
Language:English
Subjects:
Chemical Sciences
Chemistry
Cleavage reactions
Electrochemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Other
Oxidation
Protecting groups
Reactivity and mechanisms
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Summary:para‐Methoxyphenyl (PMP) ether is a very convenient protecting group for the alcohol function; however, its cleavage requires strong oxidative conditions. In this field, the use of powerful ceric ammonium nitrate has been widely described, despite the fact that its strong nature results in the formation of degradation products in acid‐ or oxidation‐sensitive substrates. In this paper, a new anodic oxidation method for the cleavage of para‐methoxyphenyl ethers in weakly basic medium is reported. This process is an attractive alternative to circumvent the use of ceric ammonium nitrate. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) Herein is reported the first anodic oxidation method for the cleavage of primary and secondary alkyl para‐methoxyphenyl ethers. Under a controlled potential (1.7 V) and in the presence of NaHCO3, this reaction tolerates oxidation and acid‐sensitive functions, thus constituting an efficientmethod for the orthogonal deprotection of para‐methoxyphenyl ethers.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200900262