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Synfacts 2013; 9(10): 1103
DOI: 10.1055/s-0033-1339822
DOI: 10.1055/s-0033-1339822
Metal-Mediated Synthesis
Cobalt–NHC-Catalyzed ortho-Alkylation of Aromatic Imines with Alkyl Halides
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
17. September 2013 (online)
Significance
A novel method for the direct ortho-alkylation of aromatic imines has been disclosed. 10 mol% of cobalt(II) bromide (CoBr2) in combination with an N-heterocyclic carbene (NHC) ligand catalyzes the reaction of an alkyl halide with the aromatic imine to deliver the corresponding ortho-alkylated ketones after acidic work-up.
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Comment
The activation of the alkyl halide is proposed to occur through single-electron transfer from a cobalt species to generate an alkyl radical. Recombination of the cobalt and the radical centers may cause the C–C bond formation.
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