Directed ortho-Metalation, a New Insight into Organosodium Chemistry We thank the Ministère de la Recherche et de l'Enseignement for MRE grants to A. Gissot and J.-M. Becht. We are also grateful to Prof. Manfred Schlosser, Lausanne, and Dr. Matteo Zanda, Milan, Italy, for helpful suggestions.

Abstract

Finely dispersed metallic sodium in combination with an alkyl chloride RCl can replace organolithium reagents in the ortho-metalation of aromatic compounds (see scheme). The in situ generated base is consumed as soon as it is formed, which avoids Wurtz coupling, the usual side reaction, and the handling and storage of highly reactive alkyl sodium bases. Reaction conditions are mild, the reaction is easy to scale up, and the reagents needed are inexpensive.