Direct transformation of esters into arenes with 1,5-bifunctional organomagnesium reagents.
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.
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel (Switzerland) http://www.chemie.unibas.ch/∼sparr.
Achim
A
Link
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel (Switzerland) http://www.chemie.unibas.ch/∼sparr.
Christian
C
Fischer
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel (Switzerland) http://www.chemie.unibas.ch/∼sparr. christof.sparr@unibas.ch.
Christof
C
Sparr
Grignard reactions; acenes; arenes; carboxylic acid esters; organomagnesium reagents