Molecules 2004, 9(5), 365-372; doi:10.3390/90500365
Article

Nucleophilic Benzoylation Using a Mandelic Acid Dioxolanone as a Synthetic Equivalent of the Benzoyl Carbanion. Oxidative Decarboxylation of α-Hydroxyacids

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Received: 5 March 2004; Accepted: 18 March 2004 / Published: 30 April 2004
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: The synthesis of alkyl aryl ketones using a mandelic acid dioxolanone as a synthetic equivalent (Umpolung) of the benzoyl carbanion is reported. The methodology involves alkylation of the mandelic acid dioxolanone, hydrolysis of the dioxolanone moiety in the alkylated products and oxidative decarboxylation of the resulting α-hydroxyacids. The last step is carried out in a catalytic aerobic way using a Co (III) complex in the presence of pivalaldehyde under very mild conditions.
Keywords: Alkylation; dioxolanone; decarboxylation; catalysts; cobalt; Umpolung.
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MDPI and ACS Style

Blay, G.; Fernández, I.; Monje, B.; Pedro, J.R. Nucleophilic Benzoylation Using a Mandelic Acid Dioxolanone as a Synthetic Equivalent of the Benzoyl Carbanion. Oxidative Decarboxylation of α-Hydroxyacids. Molecules 2004, 9, 365-372.

AMA Style

Blay G, Fernández I, Monje B, Pedro JR. Nucleophilic Benzoylation Using a Mandelic Acid Dioxolanone as a Synthetic Equivalent of the Benzoyl Carbanion. Oxidative Decarboxylation of α-Hydroxyacids. Molecules. 2004; 9(5):365-372.

Chicago/Turabian Style

Blay, Gonzalo; Fernández, Isabel; Monje, Belén; Pedro, José R. 2004. "Nucleophilic Benzoylation Using a Mandelic Acid Dioxolanone as a Synthetic Equivalent of the Benzoyl Carbanion. Oxidative Decarboxylation of α-Hydroxyacids." Molecules 9, no. 5: 365-372.

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