Qian Bai-Yu, Zhang Wei, Lin Jin-Hong, Cao Weiguo, Xiao Ji-Chang
Department of Chemistry, Innovative Drug Research Center, Shanghai University, 99 Shangda Road, Shanghai, 200444, P. R. China.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
Chem Asian J. 2022 May 2;17(9):e202200184. doi: 10.1002/asia.202200184. Epub 2022 Mar 22.
The fluorination of alkenes with electrophilic N-F type reagents usually occurs through a Markovnikov-type addition, and the anti-Markovnikov-type addition may require the use of a transition metal catalyst or an expensive catalyst. Herein we describe a convenient anti-Markovnikov iodofluorination of alkenes with Selectfluor/ Bu NI. A wide substrate scope and good functional group tolerance were observed. The process allows for the construction of various C-F bonds, especially tertiary C-F bonds. The remarkable features make this protocol attractive, including convenient operations, simple reaction conditions, and the installation of an iodine atom which provides possibilities for further transformations.
使用亲电N-F型试剂对烯烃进行氟化反应通常通过马氏加成进行，而反马氏加成可能需要使用过渡金属催化剂或昂贵的催化剂。在此，我们描述了一种使用Selectfluor/Bu NI对烯烃进行便捷的反马氏碘氟代反应。该反应具有广泛的底物范围和良好的官能团耐受性。此过程能够构建各种C-F键，尤其是叔碳C-F键。这些显著特点使得该方法具有吸引力，包括操作便捷、反应条件简单，以及引入碘原子为进一步转化提供了可能性。
