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Synfacts 2013; 9(10): 1103
DOI: 10.1055/s-0033-1339822
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Cobalt–NHC-Catalyzed ortho-Alkylation of Aromatic Imines with Alkyl Halides

Contributor(s):
Paul Knochel
,
Andreas K. Steib
Gao K, Yoshikai N * Nanyang Technology University, Singapore, Singapore
Cobalt-Catalyzed Ortho Alkylation of Aromatic Imines with Primary and Secondary Alkyl Halides.

J. Am. Chem. Soc. 2013;
135: 9279-9282
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Further Information

Publication History

Publication Date:
17 September 2013 (online)

 
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Key words

cobalt - alkylation - Grignard reagents

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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