Tan Yu-Fang, Zhao Ya-Nan, Yang Dan, Lv Jin-Feng, Guan Zhi, He Yan-Hong
Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China.
Analytical and Testing Center, Southwest University, Chongqing 400715, China.
J Org Chem. 2023 Apr 21;88(8):5161-5171. doi: 10.1021/acs.joc.2c03020. Epub 2023 Mar 28.
We report a novel and highly selective electrochemical method for the synthesis of β-iodoesters via difunctionalization of alkenes. The reaction is carried out in an undivided cell under constant current conditions without any additives, catalysts, oxidants, and sacrificial reagents. Inexpensive and readily available tetrabutylammonium iodide not only acts as an electrolyte but also serves as an iodine source. The reaction shows high selectivity and good functional group tolerance, providing products in yields of up to 98%. This method is applicable not only to the iodofunctionalization of alkenes but also to the chloro- and bromofunctionalization of alkenes. The successful modification of drugs and natural products demonstrates the potential utility of this approach.
我们报道了一种通过烯烃双官能化合成β-碘代酯的新型高选择性电化学方法。该反应在无隔膜电解池中恒流条件下进行，无需任何添加剂、催化剂、氧化剂和牺牲试剂。廉价且易于获得的四丁基碘化铵不仅作为电解质，还作为碘源。该反应具有高选择性和良好的官能团耐受性，产率高达98%。此方法不仅适用于烯烃的碘官能化，也适用于烯烃的氯官能化和溴官能化。药物和天然产物的成功修饰证明了该方法的潜在实用性。
