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DOI: 10.1055/s-0033-1338658
Cobalt-Catalyzed Chelation-Assisted Alkylation of Arenes with Primary and Secondary Alkyl Halides
Publication History
Received: 07 April 2014
Accepted after revision: 12 June 2014
Publication Date:
09 July 2014 (online)
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Abstract
Cobalt–N-heterocyclic carbene catalytic systems have been developed for chelation-assisted ortho-alkylation of aromatic compounds with alkyl halides. Aryl imines can be selectively monoalkylated at room temperature by various primary or secondary alkyl chlorides or bromides. The catalytic system can also be applied to 2-arylpyridine derivatives, which in the absence of steric hindrance are amenable to dialkylation by an excess of the alkyl halide. Mechanistic experiments, including reactions of stereochemical probes and radical clocks, indicate that the reaction involves single-electron transfer from the cobalt center to the alkyl halide to form the corresponding alkyl radical, which has a finite lifetime before it undergoes C–C bond formation.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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For recent examples, see:
For branched-selective reaction with styrene derivatives, see:
For Markovnikov-selective reaction of phenol derivatives with alkyl olefins, see:
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