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Copper-Catalyzed Cross-Coupling Reaction of Grignard Reagents with Primary-Alkyl Halides: Remarkable Effect of 1-Phenylpropyne

Authors

  • Jun Terao Dr.,

    1. Department of Applied Chemistry & Science and Technology Center for Atoms, Molecules, and Ions Control, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-7390
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  • Hirohisa Todo,

    1. Department of Applied Chemistry & Science and Technology Center for Atoms, Molecules, and Ions Control, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-7390
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  • Shameem Ara Begum,

    1. Department of Applied Chemistry & Science and Technology Center for Atoms, Molecules, and Ions Control, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-7390
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  • Hitoshi Kuniyasu Dr.,

    1. Department of Applied Chemistry & Science and Technology Center for Atoms, Molecules, and Ions Control, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-7390
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  • Nobuaki Kambe Prof. Dr.

    1. Department of Applied Chemistry & Science and Technology Center for Atoms, Molecules, and Ions Control, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-7390
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  • This study was supported by the Industrial Technology Research Grant Program in 2006 from the New Energy and Industrial Technolgy Development Organization (NEDO) of Japan and a Grant-in-Aid for Scientific Research on Priority Areas from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

Abstract

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Gelungene Verbindung: Die Cu-katalysierte Kreuzkupplung zwischen primären Alkylhalogeniden und primären, sekundären und tertiären Alkyl- sowie Phenyl-Grignard-Reagentien verläuft in THF unter Rückfluss in Gegenwart von 1-Phenylpropin effizient (siehe Schema). Die Reaktion gelingt auch mit Alkylmesylaten (OMs) und -tosylaten (OTs). Die Alkyl-X-Reaktivitäten gegenüber dem Grignard-Reagens nehmen in der Reihenfolge X=Cl<F<OMs<OTs<Br zu.

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