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.
J Org Chem. 2012 Jan 6;77(1):718-24. doi: 10.1021/jo202017z. Epub 2011 Dec 1.
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.
在没有金属催化剂的情况下，无需保护羧酸（CO(2)H）基团，1-和 2-萘酸中的邻氟或甲氧基取代基与烷基/乙烯基/芳基有机锂和格氏试剂反应，可高产至高产率地得到取代的萘酸。这种新型的亲核芳香取代反应被认为是通过有机金属与底物的预配位，然后加成/消除来进行的。
