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Synfacts 2013; 9(1): 0088
DOI: 10.1055/s-0032-1317741
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Iron-Catalyzed Hydromagnesiation of Diarylalkynes and Diynes

Contributor(s):
Paul Knochel
,
Andreas K. Steib
Ilies L, Yoshida T, Nakamura E * The University of Tokyo, Japan
Iron-Catalyzed Chemo- and Stereoselective Hydromagnesiation of Diarylalkynes and Diynes.

J. Am. Chem. Soc. 2012;
134: 16951-16954
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

iron - magnesium - alkynes

Significance

The authors report a novel iron-­catalyzed hydromagnesiation of diarylalkynes in high yield with high stereoselectivity. Furthermore, alkenyl-magnesium compounds can be synthesized from diynes in a chemo-, regio- and stereo­selective way.


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Comment

The alkenylmagnesium intermediates can further be functionalized in a one-pot sequence. Reactions with allyl bromide, N,N-dimethylformamide and even nickel-catalyzed cross-couplings have been disclosed. The authors suggest a radical mechanism instead of a pure anionic mechanism.


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