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-烷基硫代苯甲酸酯及其衍生物的选择性电化学氟化

The selective electrochemical fluorination of -alkyl benzothioate and its derivatives.

作者信息

Kuribayashi Shunsuke, Kurioka Tomoyuki, Inagi Shinsuke, Lu Ho-Jung, Uang Biing-Jiun, Fuchigami Toshio

机构信息

Department of Electronic Chemistry, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8502, Japan.

Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8502, Japan.

出版信息

Beilstein J Org Chem. 2018 Feb 12;14:389-396. doi: 10.3762/bjoc.14.27. eCollection 2018.

Abstract

We herein report that the regioselective anodic fluorination of -alkyl benzothioate and its derivatives in various aprotic solvents using EtN·HF ( = 3-5) and EtNF·HF ( = 3-5) as supporting electrolyte and a fluorine source successfully provided the corresponding α-fluorinated products in moderate yields. Dichloromethane containing EtNF·4HF was found to be the most suitable combination as electrolytic solvent and supporting salt as well as fluorine source for the anodic fluorination. The electrochemical fluorination of cyclic benzothioates such as benzothiophenone was also achieved.

摘要

我们在此报告,使用EtN·HF(n = 3 - 5)和EtNF·HF(n = 3 - 5)作为支持电解质和氟源,在各种非质子溶剂中对α-烷基苯硫酯及其衍生物进行区域选择性阳极氟化反应,成功以中等产率得到了相应的α-氟化产物。发现含有EtNF·4HF的二氯甲烷是作为电解溶剂、支持盐以及用于阳极氟化反应的氟源的最合适组合。环状苯硫酯如苯并噻吩酮的电化学氟化反应也得以实现。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/372c/5827776/a01b34444e64/Beilstein_J_Org_Chem-14-389-g002.jpg

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