title: ortho-Lithium/magnesium carboxylate-driven aromatic nucleophilic substitution reactions on unprotected naphthoic acids.
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.
authors: Unité de Chimie Organique Moléculaire et Macromoléculaire (UMR 6011), Faculté des Sciences,  Université du Maine  and CNRS, avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France.
authors: Regadia
authors: R
authors: Aissaoui
authors: Arnaud
authors: A
authors: Nourry
authors: Ariane
authors: A
authors: Coquel
authors: Thi Thanh Hà
authors: TT
authors: Dao
authors: Aicha
authors: A
authors: Derdour
authors: Jean-Jacques
authors: JJ
authors: Helesbeux
authors: Olivier
authors: O
authors: Duval
authors: Anne-Sophie
authors: AS
authors: Castanet
authors: Jacques
authors: J
authors: Mortier
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D007202:Indicators and Reagents; D008094:Lithium / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D009942:Organometallic Compounds
chemical_list: D002264:Carboxylic Acids; D007202:Indicators and Reagents; D009281:Naphthalenes; D009942:Organometallic Compounds; C085312:1-naphthoic acid; D008094:Lithium; D008274:Magnesium; C030037:2-naphthoic acid