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

Ryosuke Agata, Takahiro Iwamoto, Naohisa Nakagawa, Katsuhiro Isozaki, Takuji Hatakeyama, Hikaru Takaya, Masaharu Nakamura*

*International Research Center for Elements Science, Institute for Chemical Research (ICR), Kyoto University, Uji, Kyoto 611-0011, Japan, Email: masaharuscl.kyoto-u.ac.jp

R. Agata, T. Iwamoto, N. Nakagawa, K. Isozaki, T. Hatakeyama, H. Takaya, M. Nakamura, Synthesis, 2015, 47, 1733-1740.

DOI: 10.1055/s-0034-1380361 (free Supporting Information)


Abstract

The use of catalytic amounts of iron(III) fluoride and 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene (SIPr) enables high-yielding cross-coupling reactions of various combinations of aryl chlorides and alkyl Grignard reagents including methylmagnesium bromide.

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Cross-Coupling of Non-activated Chloroalkanes with Aryl Grignard Reagents in the Presence of Iron/N-Heterocyclic Carbene Catalysts

S. K. Ghorai, M. Jin, T. Hatakeyama, M. Nakamura, Org. Lett., 2012, 14, 1066-1069.


Key Words

C-C bond formation, cross coupling, iron fluoride, N-heterocyclic carbene, aryl chloride


ID: J66-Y2015