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

doi:10.3390/90500365

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

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

Gonzalo Blay, Isabel Fernández, Belén Monje and José R. Pedro*

Departament de Química Orgànica, Facultat de Química, Universitat de València, E-46100 Burjassot (València), Spain

* Author to whom correspondence should be addressed.

Received: 5 March 2004 / Accepted: 18 March 2004 / Published: 30 April 2004

(This article belongs to the Special Issue Carbanion chemistry from Carboxylic acids in honor of Prof. Ramón Mestres on his 65th anniversary)

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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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