Synthesis 2015; 47(12): 1733-1740
DOI: 10.1055/s-0034-1380361
paper
© Georg Thieme Verlag Stuttgart · New York

Iron Fluoride/N-Heterocyclic Carbene Catalyzed Cross Coupling­ between Deactivated Aryl Chlorides and Alkyl Grignard Reagents with or without β-Hydrogens

Ryosuke Agata
a  International Research Center for Elements Science, Institute for Chemical Research (ICR), Kyoto University, Uji, Kyoto 611-0011, Japan   Email: [email protected]
b  Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan
,
Takahiro Iwamoto
a  International Research Center for Elements Science, Institute for Chemical Research (ICR), Kyoto University, Uji, Kyoto 611-0011, Japan   Email: [email protected]
b  Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan
c  CRESTJapan Science and Technology Agency (JST), 4-1-8 Honcho Kawaguchi, Saitama 332-0012, Japan
,
Naohisa Nakagawa
a  International Research Center for Elements Science, Institute for Chemical Research (ICR), Kyoto University, Uji, Kyoto 611-0011, Japan   Email: [email protected]
b  Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan
,
Katsuhiro Isozaki
a  International Research Center for Elements Science, Institute for Chemical Research (ICR), Kyoto University, Uji, Kyoto 611-0011, Japan   Email: [email protected]
b  Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan
,
Takuji Hatakeyama
a  International Research Center for Elements Science, Institute for Chemical Research (ICR), Kyoto University, Uji, Kyoto 611-0011, Japan   Email: [email protected]
d  Elements Strategy Initiative for Catalysts and Batteries (ESICB), Kyoto University, Nishikyo-ku, Kyoto 615-8520, Japan
e  Current address: Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan
,
Hikaru Takaya
a  International Research Center for Elements Science, Institute for Chemical Research (ICR), Kyoto University, Uji, Kyoto 611-0011, Japan   Email: [email protected]
b  Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan
,
Masaharu Nakamura*
a  International Research Center for Elements Science, Institute for Chemical Research (ICR), Kyoto University, Uji, Kyoto 611-0011, Japan   Email: [email protected]
b  Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan
› Author Affiliations
Further Information

Publication History

Received: 08 January 2015

Accepted: 17 February 2015

Publication Date:
08 April 2015 (online)


Abstract

High-yielding cross-coupling reactions of various combinations of aryl chlorides and alkyl Grignard reagents have been developed by using an iron(III) fluoride/1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene (SIPr) catalyst composite. The iron(III) fluoride/SIPr-catalyzed aryl–alkyl coupling demonstrates unprecedented scope for both aryl chlorides and alkyl Grignard reagents, thus enabling the first efficient coupling of electron-rich (deactivated) aryl chlorides with alkyl Grignard­ reagents without β-hydrogens. The present reaction is also effective for diverse alkyl Grignard reagents such as (trimethylsilyl)methyl, primary, and secondary alkyl Grignard reagents.

Supporting Information

 
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