Journal
SYNTHESIS-STUTTGART
Volume 46, Issue 15, Pages 2024-2039Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1338658
Keywords
functionalization; catalysis; cobalt; alkylations; alkyl halides; radical reaction
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Funding
- Singapore National Research Foundation [NRF-RF2009-05]
- Nanyang Technological University
- JST, CREST
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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.
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