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Synfacts 2008(11): 1160-1160  
DOI: 10.1055/s-0028-1083474
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

A Mild Access to Aryl Magnesium Reagents

Contributor(s): Timothy M. Swager, Jan M. Schnorr
F. M. Piller, P. Appukkuttan, A. Gavryushin, M. Helm, P. Knochel*
Ludwig-Maximilians-Universität München, Germany
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Publication History

Publication Date:
23 October 2008 (online)

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Significance

The authors present a mild route to a variety of aryl magnesium reagents that can be directly used in Negishi cross-coupling reactions or transmetalated for other C-C cross-couplings. Halogenated (Cl or Br) aromatics or heteroaromatics were treated with Mg(0) in the presence of LiCl at temperatures between -20 and 25 ˚C for 10 minutes to three hours. Less stable magnesium reagents like ester 5 could be transformed into their zinc derivatives 6 in situ and were further used in copper- or palladium-catalyzed reactions.