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DOI: 10.1055/s-2007-968804
Non-Kolbe Electrolysis Using Solid-Supported Bases
Contributor(s):Yasuhiro Uozumi, Yutaka MatsuuraPublication History
Publication Date:
24 July 2007 (online)
Key words
electrochemical reaction - non-Kolbe electrolysis - anodic methoxylation
Significance
A novel electrolytic system for anodic methoxylation of carboxylic acids using silica gel supported bases (e.g. piperidine) was developed. Non-Kolbe electrolysis of carboxylic acid 1 proceeded smoothly to provide methoxylated product 2, which was easily isolated by simple evaporation of the filtrate after the removal of the silica gel supported piperidine. The reuse of silica gel supported piperidine was successfully carried out five times under the same conditions. The various carboxylic acids were examined to give the corresponding methoxylated products in excellent yields (5 examples, 94-100% yields).
Comment
The authors have reported an electric system for anodic methoxylation and acetoxylation of phenyl 2,2,2-trifluoroethyl sulfide using solid-supported bases (J. Am. Chem. Soc. 2005, 127, 2848; Angew. Chem. Int. Ed. 2005, 44, 4760). In this paper, they reported the electrolytic system based on the acid-base reaction between carboxylic acids and silica gel supported piperidine to realize the non-Kolbe electrolysis of carboxylic acids where the carboxylate anion served as both a substrate and a supporting electrolyte.