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Synfacts 2009(2): 0189-0189  
DOI: 10.1055/s-0028-1087658
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Mn-Catalyzed Cross-Coupling of Aryl Grignard Reagents with Alkenyl Halides

Contributor(s):Paul Knochel, Tobias Thaler
G. Cahiez*, O. Gager, F. Lecomte
Université de Paris13, Bobigny, France
Manganese-Catalyzed Cross-Coupling Reaction Between Aryl Grignard Reagents and Alkenyl Halides
Org. Lett.  2008,  10:  5255-5256  
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Publication History

Publication Date:
22 January 2009 (online)

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Key words

manganese catalysis - cross-coupling - stereoselectivity - aryl Grignard reagents - alkenyl halides

Significance

In this article a highly stereoselective Mn(II)-catalyzed cross-coupling reaction between (hetero)aryl Grignard reagents and non-­activated alkenyl halides is reported. The stereo­information of the alkenyl halide is usually preserved. An exception to that rule represents the case of (Z)-3-(2-bromoethenyl)pyridine, where the configuration of the double bond is completely ­reversed.

Comment

This new methodology shows that also Mn(II) salts can be successfully used as catalysts in cross-coupling reactions with non-activated electrophiles. Mn-catalyzed reactions represent a real alternative to Fe-catalyzed reactions, since Mn salts are generally readily available, cheap and environmentally benign.

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