Behera Mousumi, Dharpure Pankaj D, Sahu Ajit K, Bhat Ramakrishna G
Department of Chemistry, Indian Institute of Science Education and Research (IISER)-Pune, Dr. Homi Bhabha Road, Pashan, 411008 Pune, Maharashtra, India.
J Org Chem. 2024 Oct 18;89(20):14695-14709. doi: 10.1021/acs.joc.4c00967. Epub 2024 Oct 8.
Herein, we report a mild transition metal-free organophotoredox-catalyzed approach for β-hydroxytrifluoromethylation of unactivated alkenes using CFSONa 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.
在此，我们报道了一种温和的无过渡金属有机光氧化还原催化方法，该方法使用CFSONa和吖啶鎓盐对未活化的烯烃进行β-羟基三氟甲基化反应。该方案适用于各种含有众多官能团和天然产物衍生物的单取代、二取代和三取代脂肪族未活化烯烃。此外，通过交叉偶联和官能团互变反应证明了合成的三氟甲基化产物的后合成修饰。该方法被证明具有可扩展性，并且在阳光直接照射下能顺利进行。基于荧光猝灭实验和循环伏安分析提出了一种合理的机理。
