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Cobalt-Catalyzed Trimethylsilylmethylmagnesium-Promoted Radical Alkenylation of Alkyl Halides:  A Complement to the Heck Reaction

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    Cobalt-Catalyzed Trimethylsilylmethylmagnesium-Promoted Radical Alkenylation of Alkyl Halides:  A Complement to the Heck Reaction
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    Contribution from the Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, and Department of Chemistry, Graduate School of Science, Hiroshima University, Kagamiyama 1-3-1, Higashi-Hiroshima, Hiroshima 739-8526, Japan
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    Cite this: J. Am. Chem. Soc. 2006, 128, 24, 8068–8077
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    https://doi.org/10.1021/ja061417t
    Published May 28, 2006
    Copyright © 2006 American Chemical Society
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    Abstract

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    A cobalt complex, [CoCl2(dpph)] (DPPH = [1,6-bis(diphenylphosphino)hexane]), catalyzes an intermolecular styrylation reaction of alkyl halides in the presence of Me3SiCH2MgCl in ether to yield β-alkylstyrenes. A variety of alkyl halides including alkyl chlorides can participate in the styrylation. A radical mechanism is strongly suggested for the styrylation reaction. The sequential isomerization/styrylation reactions of cyclopropylmethyl bromide and 6-bromo-1-hexene provide evidence of the radical mechanism. Crystallographic and spectroscopic investigations on cobalt complexes reveal that the reaction would begin with single electron transfer from an electron-rich (diphosphine)bis(trimethylsilylmethyl)cobalt(II) complex followed by reductive elimination to yield 1,2-bis(trimethylsilyl)ethane and a (diphosphine)cobalt(I) complex. The combination of [CoCl2(dppb)] (DPPB = [1,4-bis(diphenylphosphino)butane]) catalyst and Me3SiCH2MgCl induces intramolecular Heck-type cyclization reactions of 6-halo-1-hexenes via a radical process. On the other hand, the intramolecular cyclization of the prenyl ether of 2-iodophenol would proceed in a fashion similar to the conventional palladium-catalyzed transformation. The nonradical oxidative addition of carbon(sp2)−halogen bonds to cobalt is separately verified by a cobalt-catalyzed cross-coupling reaction of alkenyl halides with Me3SiCH2MgCl with retention of configuration of the starting vinyl halides. The cobalt-catalyzed intermolecular radical styrylation reaction of alkyl halides is applied to stereoselective variants. Styrylations of 1-alkoxy-2-bromocyclopentane derivatives provide trans-1-alkoxy-2-styrylcyclopentane skeletons, one of which is optically pure.

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    †

     Kyoto University.

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    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

    ‡

     Hiroshima University.

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    Experimental details, characterization data for new compounds, and UV−visible spectra of cobalt complexes (PDF), and crystallographic data of [CoCl2(dpph)]2 (CIF). This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Am. Chem. Soc. 2006, 128, 24, 8068–8077
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