Shenzhen Grubbs Institute, Department of Chemistry, and Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, Guangdong, P. R. China.
Chem Commun (Camb). 2022 Jan 25;58(8):1066-1077. doi: 10.1039/d1cc06446k.
Fluorine-containing molecules have found broad applications in pharmaceutical and agrochemical industries as introducing fluorine into a molecule could significantly tune the biological activities of parent molecules. Thus, the synthesis of fluorine-containing molecules has received substantial attention over the past few decades. As a complementary strategy for the synthesis of fluorinated compounds through new C-F bonds formation, selective cleavage of inert C-F bonds from easily-available and cost-effective multifluorinated molecules, such as fluoroalkylaromatics, α-trifluoromethyl alkenes and α-multifluorinated carbonyl compounds, has been emerging as an attractive alternative to access fluorine-containing molecules. Moreover, the inherent nature of radical reactions offers the opportunity for the selective C-F functionalizations to occur under mild conditions. In this regard, the development of photoredox catalysis, transition-metal catalysis, or electrochemistry to enable radical species generation selective C-F cleavage has gained broad attention and substantial progress has been made over recent years. This highlight summerizes the recent advances in the single-electron-transfer enabled selective functionalizations of C-F bonds in multifluorinated compounds radical pathways.
含氟分子在制药和农化工业中有着广泛的应用,因为在分子中引入氟原子可以显著调节母体分子的生物活性。因此,在过去的几十年中,含氟分子的合成受到了广泛关注。作为通过新的 C-F 键形成合成氟化化合物的补充策略,从易得且具有成本效益的多氟分子(如氟烷基芳烃、α-三氟甲基烯烃和α-多氟羰基化合物)中选择性地断裂惰性 C-F 键,已经成为获得含氟分子的一种有吸引力的替代方法。此外,自由基反应的固有性质为在温和条件下发生选择性 C-F 官能化提供了机会。在这方面,开发光氧化还原催化、过渡金属催化或电化学来实现自由基物种的生成和选择性 C-F 键的断裂已经引起了广泛关注,近年来也取得了实质性的进展。本综述总结了近年来在多氟化合物中单电子转移促进的 C-F 键选择性功能化和自由基途径方面的最新进展。