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Pure Appl. Chem., 2010, Vol. 82, No. 7, pp. 1545-1553

Published online 2010-05-02

On direct iron-catalyzed cross-coupling reactions

Waldemar Maximilian Czaplik, Matthias Mayer, Sabine Grupe and Axel Jacobi von Wangelin*

Department of Chemistry, University of Cologne, Greinstrasse 4, 50939 Koeln, Germany

Abstract: A new methodology for the direct cross-coupling reaction between aryl halides and alkyl halides under iron catalysis is described. Unlike conventional protocols, the direct cross-coupling obviates the need for the preformation of stoichiometric amounts of Grignard species and thus exhibits a reduced hazard potential. The underlying one-pot reaction involves iron-catalyzed Grignard formation followed by a rapid cross-coupling step. Mechanistic data on the role of N,N,N',N'-tetramethylethylenediamine (TMEDA) as additive, the concentration of intermediates, and the nature of the catalyst species are discussed.