Direct α-Monofluoroalkenylation of Heteroatomic Alkanes via a Combination of Photoredox Catalysis and Hydrogen-Atom-Transfer Catalysis

被引：64
作者：
Tian, Hao [1 ]
Xia, Qing [1 ]
Wang, Qiang [1 ]
Dong, Jianyang [1 ]
Liu, Yuxiu [1 ]
Wang, Qingmin [1 ,2 ]
机构：
[1] Nankai Univ, Coll Chem, Res Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 12期
基金：
中国国家自然科学基金;
关键词：
C-H BONDS; FLUORINE; PHARMACEUTICALS; FLUOROOLEFINS; ALKYLATION; ARYLATION; ADDITIONS; MIMICS;
D O I：
10.1021/acs.orglett.9b01491
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this study, a new C(sp(3))-H monofluoroalkenylation reaction involving cooperative visible-light photoredox catalysis and hydrogen-atom-transfer catalysis to afford products generated by selective hydrogen abstraction and radical-radical cross-coupling was described. This mild, efficient reaction shows high regioselectivity for the alpha-carbon atoms of amines, ethers, and thioethers and thus allows the preparation of monofluoroalkenes bearing various substituents. The reaction was applied to two bioactive molecules, indicating its utility for late-stage monofluoroalkenylation of compounds with inert C(sp(3))-H bonds.
引用
收藏
页码：4585 / 4589
页数：5
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