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光氧化还原催化的未活化烯烃的分子内氟烷基化反应。

Photoredox Catalyzed Intramolecular Fluoroalkylarylation of Unactivated Alkenes.

机构信息

Department of Chemistry, University of Florida , Gainesville, Florida 32611-7200, United States.

出版信息

J Org Chem. 2017 Mar 3;82(5):2589-2598. doi: 10.1021/acs.joc.6b03012. Epub 2017 Feb 21.

Abstract

The first example of photoredox catalyzed difluoromethylation of unactivated alkenes coupled with C-C bond formation to an aryl ring is reported. The reactions are conducted under mild conditions and afford tetralin derivatives bearing difluoromethyl as well as other fluoroalkyl groups in good to high yields. In addition, the study indicates that 6-exo radical cyclization of an alkyl radical to a phenyl ring is faster than the respective 5-exo radical cyclization. A computational study provides insights to the experimental results.

摘要

首次报道了光氧化还原催化的未活化烯烃的双氟甲基化与 C-C 键形成芳环偶联的反应。该反应在温和条件下进行,以良好至高产率得到了带有双氟甲基和其他氟烷基的四氢萘衍生物。此外,该研究表明,烷基自由基到苯基环的 6-endo 自由基环化比相应的 5-exo 自由基环化更快。计算研究为实验结果提供了深入的见解。

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