Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/103795
Title: Cobalt-catalyzed chelation-assisted alkylation of arenes with primary and secondary alkyl halides
Authors: Gao, Ke
Yamakawa, Takeshi
Yoshikai, Naohiko
Keywords: DRNTU::Science::Chemistry::Organic chemistry
Issue Date: 2014
Source: Gao, K., Yamakawa, T., & Yoshikai, N. (2014). Cobalt-catalyzed chelation-assisted alkylation of arenes with primary and secondary alkyl halides. Synthesis, 46(15), 2024-2039.
Series/Report no.: Synthesis
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.
URI: https://hdl.handle.net/10356/103795
http://hdl.handle.net/10220/24559
DOI: http://dx.doi.org/10.1055/s-0033-1338658
Rights: © 2014 Georg Thieme Verlag Stuttgart. This is the author created version of a work that has been peer reviewed and accepted for publication by Synthesis, Georg Thieme Verlag Stuttgart. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1055/s-0033-1338658].
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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