Integrated Electrochemical-Chemical Oxidation Mediated by Alkoxysulfonium Ions

被引：114

作者：

Ashikari, Yosuke ^{[1
]}

Nokami, Toshiki ^{[1
]}

Yoshida, Jun-ichi ^{[1
]}

机构：

[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Grad Sch Engn, Nishikyo Ku, Kyoto 6158510, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 31期

关键词：

OLEFIN COUPLING REACTIONS; CATION-POOL METHOD; MULTICOMPONENT REACTIONS; ANODIC OXIDATIONS; ORGANIC-SYNTHESIS; TANDEM CATALYSIS; DOMINO REACTIONS; GENERATION; POT; CARBON;

D O I：

10.1021/ja202880n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Generation of carbocations by the "cation pool" method followed by reaction with dimethyl sulfoxide (DMSO) gave the corresponding alkoxysulfonium ions. Alkoxysulfonium ions could also be generated by in situ DMSO trapping of electrochemically generated carbocations. The resulting alkoxysulfonium ions were transformed into carbonyl compounds by treatment with triethylamine. The present integrated electrochemical chemical oxidation can be applied to the oxidation of diarylmethanes to diaryl ketones, toluenes to benzaldehydes, and aryl-substituted alkenes to 1,2-diketones. Moreover, the oxidation of unsaturated compounds bearing a nucleophilic group in an appropriate position gives cyclized carbonyl compounds.

引用

页码：11840 / 11843

页数：4

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