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

Molecules

Gonzalo Blay¹  Isabel Fernández¹  Belén Monje¹ 

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

关键词: Alkylation;    dioxolanone;    decarboxylation;    catalysts;    cobalt;    Umpolung.;   

DOI  :  10.3390/90500365

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.