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Mn-Catalyzed Cross-Coupling of Aryl Grignard Reagents with Alkenyl HalidesContributor(s):Paul Knochel, Tobias Thaler
Université de Paris13, Bobigny, France
Manganese-Catalyzed Cross-Coupling Reaction Between Aryl Grignard Reagents and Alkenyl Halides
Org. Lett. 2008, 10: 5255-5256
22 January 2009 (online)
manganese catalysis - cross-coupling - stereoselectivity - aryl Grignard reagents - alkenyl halides
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.
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.