Nucleophilic benzoylation using a mandelic acid dioxolanone as a synthetic equivalent of the benzoyl carbanion. Oxidative decarboxylation of alpha-hydroxyacids.
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 alpha-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.
Blay
Gonzalo
G
Departament de Química Orgànica, Facultat de Química, Universitat de València, E-46100 Burjassot (València), Spain.
Fernández
Isabel
I
Monje
Belén
B
Pedro
José R
JR
D000478:Alkylation; D019817:Benzoic Acid / Q000737:chemistry; D002254:Carbonates / Q000138:chemical synthesis / Q000737:chemistry*; D003653:Decarboxylation; D004148:Dioxolanes / Q000737:chemistry; D006880:Hydroxy Acids / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D008333:Mandelic Acids / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
D002254:Carbonates; D004148:Dioxolanes; D006880:Hydroxy Acids; D007659:Ketones; D008333:Mandelic Acids; D019817:Benzoic Acid; C037938:mandelic acid