钯催化N-磺酰基吲哚衍生物碳氢键芳基化反应  

Pd-catalyzed C—H arylation of N-sulfonyl indole derivatives

作　　者：谭晶 孙美娇 吴文倩 彭进松[1] 陈春霞[1] TAN Jing;SUN Meijiao;WU Wenqian;PENG Jinsong;CHEN Chunxia(College of Chemistry,Chemical Engineering and Resource Utilization,Northeast Forestry University,Harbin 150040,Heilongjiang,China)

机构地区：[1]东北林业大学化学化工与资源利用学院,黑龙江哈尔滨150040

出　　处：《精细化工》2024年第1期147-158,232,共13页Fine Chemicals

基　　金：黑龙江省自然科学基金项目(ZD2021C001)。

摘　　要：以碘代芳烃为芳基化试剂,探讨了N-对甲苯磺酰基吲哚通过磺酰基团导向的钯催化C—H键选择性芳基化反应过程。结果表明,以醋酸钯为催化剂、三苯基膦为配体、碳酸钠为碱、碳酸银为添加剂的条件下,N-对甲苯磺酰基吲哚在1,4-二氧六环溶剂中于120℃下反应24 h可获得2位和2,7位芳基化的产物,反应总产率可达93%。在该条件下,通过改变底物和碘代芳烃的结构测试了该法的适用范围与局限性,共制备得到28种芳基化吲哚衍生物,总产率为22%~93%,产物经~1HNMR、^(13)CNMR和HRMS表征确定了其化学结构。The sulfonyl-directing group guided and palladium catalyzed selective C—H arylation of N-p-toluenesulfonyl indole was investigated using iodoaromatic hydrocarbons as arylation reagent.The results showed that N-p-toluenesulfonyl indole could be converted into 2-and 2,7-arylated products with an overall yield of 93%in 1,4-dioxane at 120℃for 24 h with palladium acetate as catalyst,triphenylphosphine as ligand,Na_2CO_(3) as base and Ag_2CO_(3) as additive.Under these optimized conditions,the applicability and limitation of the synthetic method were examined by changing the structure of the reaction substrate and aryl iodides.As a result,28 indole-based compounds with overall yields ranging from 22%~93%were synthesized,and characterized by ~1HNMR,~(13)CNMR and HRMS spectra for structure confirmation.

关 键 词：钯催化 吲哚骨架 C—H官能化 芳基化 导向基团 催化技术 

分 类 号：TQ426[化学工程] O641.4[理学—物理化学]