ortho-Lithium/Magnesium Carboxylate-Driven Aromatic Nucleophilic Substitution Reactions on Unprotected Naphthoic Acids

…, O Duval, AS Castanet, J Mortier

Index: Le, Tin Thanh; Chau, Nguyet Trang Thanh; Nguyen, Tai Tan; Brien, Josselin; Thai, Trieu Tien; Nourry, Arnaud; Castanet, Anne-Sophie; Nguyen, Kim Phi Phung; Mortier, Jacques Journal of Organic Chemistry, 2011 , vol. 76, # 2 p. 601 - 608

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Citation Number: 6

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 (CO2H) group. This novel nucleophilic aromatic substitution is presumed to proceed via a precoordination of the organometallic with the ...