Visible Light-Induced Organophotoredox-Catalyzed β-Hydroxytrifluoromethylation of Unactivated Alkenes

被引:0
|
作者
Behera, Mousumi [1 ]
Dharpure, Pankaj D. [1 ]
Sahu, Ajit K. [1 ]
Bhat, Ramakrishna G. [1 ]
机构
[1] Indian Inst Sci Educ & Res IISER Pune, Dept Chem, Pune 411008, Maharashtra, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 20期
关键词
PHOTOREDOX CATALYSIS; TRIFLUOROMETHYLATION REACTIONS; OXYTRIFLUOROMETHYLATION; DIFUNCTIONALIZATION; CHEMISTRY; FLUORINE;
D O I
10.1021/acs.joc.4c00967
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report a mild transition metal-free organophotoredox-catalyzed approach for beta-hydroxytrifluoromethylation of unactivated alkenes using CF3SO2Na and acridinium salt. The protocol is compatible with various mono-, di-, and trisubstituted aliphatic unactivated alkenes containing numerous functional groups and natural product derivatives. Further, the postsynthetic modifications of the synthesized trifluoromethylated products have been demonstrated through cross-coupling and functional group interconversion reactions. The method proved to be scalable and it works smoothly under the direct exposure of sunlight. A plausible mechanism has been proposed based on the fluorescence quenching experiment and cyclic voltammetry analysis.
引用
收藏
页码:14695 / 14709
页数:15
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