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.
Original language | English |
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Article number | ss-2014-z0228-fa |
Pages (from-to) | 2024-2039 |
Number of pages | 16 |
Journal | Synthesis (Germany) |
Volume | 46 |
Issue number | 15 |
DOIs | |
Publication status | Published - 2014 Aug |
Externally published | Yes |
Keywords
- alkyl halides
- alkylations
- catalysis
- cobalt
- functionalization
- radical reaction
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry