Activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(sp3)-H amidation, C(sp2)-H iodination, and perfluoroalkylation reactions

CC BY-NC 3.0 UnportedWang, YaxinCao, ZehuiHe, QinHuang, XinLiu, JiaxiNeumann, HelfriedChen, GongBeller, Matthias2023-06-022023-06-022023https://oa.tib.eu/renate/handle/123456789/12252http://dx.doi.org/10.34657/11284A simple, efficient, and convenient activation of perfluoroalkyl iodides by tBuONa or KOH, without expensive photo- or transition metal catalysts, allows the promotion of versatile a-sp3 C-H amidation reactions of alkyl ethers and benzylic hydrocarbons, C-H iodination of heteroaryl compounds, and perfluoroalkylations of electron-rich p bonds. Mechanistic studies show that these novel protocols are based on the halogen bond interaction between perfluoroalkyl iodides and tBuONa or KOH, which promote homolysis of perfluoroalkyl iodides under mild conditions.enghttps://creativecommons.org/licenses/by-nc/3.0540homolytic aromatic-substitutiontransfer radical-additionc-h iodinationphotoredox catalysisaryl halidestrifluoromethylationorganocatalysisthermodynamicsheterocyclesheteroatomActivation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(sp3)-H amidation, C(sp2)-H iodination, and perfluoroalkylation reactionsArticle