Electrochemical C(sp3)-H Fluorination

被引:72
作者
Takahira, Yusuke [1 ]
Chen, Miao [1 ]
Kawamata, Yu [1 ]
Mykhailiuk, Pavel [1 ,2 ,3 ]
Nakamura, Hugh [1 ]
Peters, Byron K. [1 ]
Reisberg, Solomon H. [1 ]
Li, Chao [1 ]
Chen, Longrui [4 ]
Hoshikawa, Tamaki [5 ]
Shibuguchi, Tomoyuki [5 ]
Baran, Phil S. [1 ]
机构
[1] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
[2] Enamine Ltd, Chervonotkatska 78, UA-02094 Kiev, Ukraine
[3] Taras Shevchenko Natl Univ Kyiv, Chem Dept, Volodymyrska 64, UA-01601 Kiev, Ukraine
[4] Asymchem Life Sci Tianjin, Tianjin Econ Technol Dev Zone, Tianjin 300457, Peoples R China
[5] Eisai & Co Ltd, Discovery, Med Creat, Neurol Business Grp, 5-1-3 Tokodai, Tsukuba, Ibaraki 3002635, Japan
基金
瑞典研究理事会; 美国国家科学基金会;
关键词
organic synthesis; electrochemistry; fluorination; C-H functionalization; radicals; C-H BONDS; OXIDATION; NITRATE;
D O I
10.1055/s-0037-1611737
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and robust method for electrochemical alkyl C-H fluorination is presented. Using a simple nitrate additive, a widely available fluorine source (Selectfluor), and carbon-based electrodes, a wide variety of activated and unactivated C-H bonds are converted into their C-F congeners. The scalability of the reaction is also demonstrated with a 100 gram preparation of fluorovaline.
引用
收藏
页码:1178 / 1182
页数:5
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