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
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.
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.
