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■ The Halogen/Magnesium-Exchange Using iPrMgCl·LiCl and Related Exchange Reagents

Nadja M. Barl, Veronika Werner, Christoph Sämann, and Paul Knochel*

*Department of Chemistry, Institute of Organic Chemistry, Ludwig-Maximilians-University of Munich, Butenandtstr. 5-13 Haus F, D-81377 Munich, Germany

Abstract

We have described the regio- and chemoselective preparation of various (hetero)aryl-Grignard reagents via halogen/magnesium-exchange along with applications of these organometallics in various reactions. The LiCl-mediated halogen/magnesium-exchange proceeds readily under mild conditions and offers the opportunity to convert not only organic iodides, but less activated organic bromides, as well. Furthermore, this exchange tolerates a broad spectrum of sensitive functionalities such as triazenes, methyl esters, silylated cyanohydrins, alcohols and acrylates. Electron-rich aryl derivatives can be converted into the corresponding Mg-species by using more activated bis-alkylmagnesium compounds. Subsequent functionalization reactions such as cross-couplings, allylations, acylations, addition reactions to ketones, cyclization reactions, fluorinations, disulfenylations, aminations as well as sulfoxide/magnesium-exchange reactions have been performed, readily furnishing highly functionalized derivatives as well as biologically active heterocycles.