Chemistry Letters

Controlling chemoselectivity in reactions of unprotected naphthalene-1-carboxylic acid with strong bases

D Tilly, AS Castanet, J Mortier

Index: Tilly, David; Castanet, Anne-Sophie; Mortier, Jacques Chemistry Letters, 2005 , vol. 34, # 3 p. 446 - 447

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Citation Number: 12

Abstract

Whereas treatment of unprotected naphthalene-1-carboxylic acid with alkyllithiums (RLi) affords 1, 4-addition products, the reaction with LTMP/Me 3 SiCl under in situ quench conditions provides the arylsilane arising out from the substitution of lithium 2- lithionaphthalene carboxylate with Me 3 SiCl. With the Lochmann–Schlosser superbase (n- BuLi/t-BuOK), metalation occurs preferentially in the position adjacent to CO 2 Li although ...