Journal of Organic Chemistry 2012-01-06

ortho-Lithium/magnesium carboxylate-driven aromatic nucleophilic substitution reactions on unprotected naphthoic acids.

Regadia Aissaoui, Arnaud Nourry, Ariane Coquel, Thi Thanh Hà Dao, Aicha Derdour, Jean-Jacques Helesbeux, Olivier Duval, Anne-Sophie Castanet, Jacques Mortier

Index: J. Org. Chem. 77(1) , 718-24, (2012)

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Abstract

Substitution of an ortho-fluoro or methoxy group in 1- and 2-naphthoic acids furnishing substituted naphthoic acids occurs in good to excellent yields upon reaction with alkyl/vinyl/aryl organolithium and Grignard reagents, in the absence of a metal catalyst without the need to protect the carboxyl (CO(2)H) group. This novel nucleophilic aromatic substitution is presumed to proceed via a precoordination of the organometallic with the substrate, followed by an addition/elimination.