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Highly Regio- and Stereoselective Synthesis of Multialkylated Olefins through Carbozirconation of Alkynylboronates and Sequential Negishi and Suzuki–Miyaura Coupling Reactions

Authors

  • Prof. Dr. Yasushi Nishihara,

    Corresponding author
    1. Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530 (Japan)
    • Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530 (Japan)
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  • Yoshiaki Okada,

    1. Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530 (Japan)
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  • Jiao Jiao,

    1. Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530 (Japan)
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  • Masato Suetsugu,

    1. Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530 (Japan)
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  • Ming-Tzu Lan,

    1. Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530 (Japan)
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  • Megumi Kinoshita,

    1. Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530 (Japan)
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  • Prof. Dr. Masayuki Iwasaki,

    1. Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530 (Japan)
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  • Prof. Dr. Kentaro Takagi

    1. Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530 (Japan)
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  • We gratefully thank Prof. Hiroshi Nakazawa and Dr. Masumi Itazaki at Osaka City University for measurements of elemental analyses and Prof. Tamotsu Takahashi at Hokkaido University for generous donation of zirconocene dichloride. This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas “Advanced Molecular Transformations of Carbon Resources” from the Ministry of Education, Culture, Sports, Science and Technology (Japan).

Abstract

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Two Nobel couplings: The synthesis of tri- and tetraalkylated olefins has been achieved (see scheme). These multialkylated olefins were prepared by the zirconocene-mediated carbometalation of 1-alkynylboronates and subsequent sequential C[BOND]C bond formation with Negishi and Suzuki–Miyaura cross-coupling reactions using β-hydrogen-containing alkylzinc reagents and alkyl electrophiles as coupling partners.

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