Direct Transformation of Esters into Arenes with 1,5-Bifunctional Organomagnesium Reagents.

Angewandte Chemie (International ed. in English)

PubMedID: 26291060

Link A, Fischer C, Sparr C. Direct Transformation of Esters into Arenes with 1,5-Bifunctional Organomagnesium Reagents. Angew Chem Int Ed Engl. 2015;.
A direct transformation of carboxylic acid esters into arenes with 1,5-bifunctional organomagnesium reagents is described. This efficient and practical method enables the one-step defunctionalization of various carboxylic acid esters to prepare benzene, anthracene, tetracene, and pentacene derivatives. A double nucleophilic addition of the 1,5-organodimagnesium reagent to the ester is followed by an immediate 1,4-elimination reaction that leads to the direct [5+1] formation of a new aromatic ring.