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Issue 16, 2010
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The fine balance between one cross-coupling and two β-hydride elimination pathways: a DFT mechanistic study of Ni(π-allyl)2-catalyzed cross-coupling of alkyl halides and alkyl Grignard reagents

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Abstract

The model cross-coupling of EtBr with EtMgCl mediated by Ni(π-allyl)2 proceeds by a catalytic cycle commencing with transmetalation establishing a novel Mgallyl interaction, followed by Mg-assisted oxidative addition (the rate-determining step), followed by reductive elimination having much lower barrier than 2 competing β-hydride elimination pathways, and completed by departure of MgBrCl.

Graphical abstract: The fine balance between one cross-coupling and two β-hydride elimination pathways: a DFT mechanistic study of Ni(π-allyl)2-catalyzed cross-coupling of alkyl halides and alkyl Grignard reagents

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Publication details

The article was received on 26 Oct 2009, accepted on 25 Nov 2009 and first published on 16 Dec 2009


Article type: Communication
DOI: 10.1039/B922326F
Citation: Chem. Commun., 2010,46, 2727-2729
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    The fine balance between one cross-coupling and two β-hydride elimination pathways: a DFT mechanistic study of Ni(π-allyl)2-catalyzed cross-coupling of alkyl halides and alkyl Grignard reagents

    G. A. Chass, E. A. B. Kantchev and D. Fang, Chem. Commun., 2010, 46, 2727
    DOI: 10.1039/B922326F

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