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Synfacts 2019; 15(06): 0641
DOI: 10.1055/s-0037-1612544
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Iron-Catalyzed Alkenylation of Organomagnesium Reagents

Contributor(s):
Paul Knochel
,
Moritz Balkenhohl
Cahiez G. * Avedissian H. Ecole Supérieure de Chimie Organique et Minérale, Cergy-Pontoise, France
Highly Stereo- and Chemoselective Iron-Catalyzed Alkenylation of Organomagnesium Compounds.

Synthesis 1998; 1199-1205
Article in Thieme ConnectGoogle Scholar
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Publication History

Publication Date:
20 May 2019 (online)

 
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Key words

cross-coupling - iron catalysis - magnesium

Significance

In 1998, Cahiez and Avedissian reported a general method for the iron-catalyzed cross-coupling between alkenyl halides (halide = Cl, Br, or I) and Grignard reagents in high yields and excellent diastereoselectivities (>99:1).


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Comment

The approach significantly improved the cross-coupling between alkenyl halides and ­Grignard reagents using Fe(acac)3 as catalyst. Additionally, it was found that the use of a polar co-solvent such as NMP was crucial for the cross-coupling to proceed in excellent yields. Furthermore, functional groups such as ketones were tolerated for the first time in these cross-coupling reactions (see Review below).


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Review

C. Bolm, J. Legros, J. Le Paih, L. Zani Chem. Rev. 2004, 104, 6217–6254.


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