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Issue 6, 2003
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Kumada–Corriu coupling of Grignard reagents, probed with a chiral Grignard reagent

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Abstract

The Grignard reagent 2, in which the magnesium-bearing carbon atom is the sole stereogenic centre has been coupled with vinyl bromide under Pd(0) or Ni(0)-catalysis to give compound 3 with full retention of configuration. Coupling using Fe(acac)3 or Co(acac)2 as catalyst was accompanied by considerable racemisation. These findings are discussed with respect to a dichotomy between concerted polar and stepwise SET transmetallation pathways.

Graphical abstract: Kumada–Corriu coupling of Grignard reagents, probed with a chiral Grignard reagent

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Publication details

The article was received on 02 Jan 2003, accepted on 29 Jan 2003 and first published on 19 Feb 2003


Article type: Communication
DOI: 10.1039/B300033H
Citation: Chem. Commun., 2003,0, 732-733
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    Kumada–Corriu coupling of Grignard reagents, probed with a chiral Grignard reagent

    B. Hölzer and R. W. Hoffmann, Chem. Commun., 2003, 0, 732
    DOI: 10.1039/B300033H

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