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Issue 11, 2008
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A new approach to anodic substitution reaction using acoustic emulsification

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Abstract

We have developed a novel electrolytic system for anodic substitution reactions using acoustic emulsification. This new system involves the generation of a carbocation by anodic oxidation of a substrate, and then its reaction with a nucleophile droplet formed by ultrasonication. In this system, even if the oxidation potential of the nucleophile is lower than that of the substrate, the substrate was predominantly oxidized to give the corresponding cation intermediate because the nucleophile phase, which was insoluble in the electrolytic medium, was electro-inactive. In addition, the overoxidation of the desired products was considerably suppressed by the extraction of products from the electrolyte solution into the nucleophile phase. As a result, the anodic substitution reaction of several carbamates with allyltrimethylsilane was carried out to provide the corresponding products in good to moderate yields.

Graphical abstract: A new approach to anodic substitution reaction using acoustic emulsification

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Article information


Submitted
20 Feb 2008
Accepted
07 Mar 2008
First published
09 Apr 2008

Org. Biomol. Chem., 2008,6, 1938-1943
Article type
Paper

A new approach to anodic substitution reaction using acoustic emulsification

R. Asami, T. Fuchigami and M. Atobe, Org. Biomol. Chem., 2008, 6, 1938
DOI: 10.1039/B802961J

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