Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Institute of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, P. R. China.
School of Chemistry and Chemical Engineering, Yan'an University, Yan'an 716000, P. R. China.
Org Biomol Chem. 2022 Apr 6;20(14):2857-2862. doi: 10.1039/d2ob00453d.
The pyridine/bis(pinacolate)diboron combination has been found to be able to initiate the iodoperfluoroalkylation of unactivated alkenes with perfluoroalkyl iodides. Theoretical calculations and control experiments indicate that the atom transfer radical addition mechanism is responsible for the formation of iodoperfluoroalkylation products. This metal-free and photo-free strategy is applicable to a wide range of perfluoroalkyl iodides and unactivated alkenes with good functional group tolerance. Further applications in iodoperfluoroalkylation of organic semiconductor-relevant or bioactive molecules demonstrate the synthetic potential of this method.
吡啶/双(频哪醇)二硼组合已被发现能够引发未活化烯烃与全氟碘代烷的碘代全氟烷基化反应。理论计算和对照实验表明，原子转移自由基加成机理负责形成碘代全氟烷基化产物。这种无金属和无光的策略适用于广泛的全氟碘代烷和未活化烯烃，具有良好的官能团容忍度。该方法在有机半导体相关或生物活性分子的碘代全氟烷基化中的进一步应用证明了该方法的合成潜力。
