铑催化吲哚导向芳烃与氮杂苯并冰片烯的加成开环反应  

Rhodium-catalyzed ring-opening reaction of indole-directed arenes with azabenzonorbornadienes

作　　者：邓耀 陈景超[1] 刘子秀 李泓江 周冰洁 樊保敏[1,2] Yao Deng;Jingchao Chen;Zixiu Liu;Hongjiang Li;Bingjie Zhou;Baomin Fan(Key Laboratory of Chemistry in Ethnic Medicinal Resources,State Ethnic Afairs Commssion&Ministry of Education,Yunnan Minzu University Kunming 650500,China;School of Chemistry and Environment,Yunnan Minzu University,Kunming 650500,China)

机构地区：[1]云南民族大学民族药资源化学教育部重点实验室,昆明650500 [2]云南民族大学化学与环境学院,昆明650500

出　　处：《中国科学：化学》2023年第9期1735-1740,共6页SCIENTIA SINICA Chimica

基　　金：国家自然科学基金(编号:21961045,22061048)资助项目。

摘　　要：碳氢键的直接官能团化已成为有机合成中构筑碳碳键的一种高效方法.这种转化不需要预官能团化,被认为是原子步骤经济的合成途径.在不同导向基辅助过渡金属催化下,区域选择性碳氢官能团化为C–C和C–X键的构建提供了一种简洁的方法.Rh(Ⅲ)催化氮杂苯并冰片烯C–H活化开环反应已有研究,但反应体系中通常需要添加氧化剂或者反应条件苛刻.本文开发了2-芳基吲哚与氮杂苯并降冰片烯的开环反应研究.该反应体系无需氧化剂,化学区域选择性高,官能团兼容性好,条件温和,反应产率高达98%,为2-芳基氢化萘衍生物的合成提供了高效便捷的方法.The direct functionalization of C-H bonds has become an efficient method for constructing carbon-carbon bonds in organic synthesis.As the transformation does not require pre-functionalization,it is regarded as the atomeconomic and step-economic method.The transition metal catalyzed selective C-H functionalization provides a concise method for the construction of C-C and C-X bonds.Although the Rh(Il)-catalyzed ring-opening reactions of azabenzonorbornadienes via C-H activation have been studied,the reactions usually require the addition of oxidant or harsh reaction conditions.Herein,we develop the ring-opening reactions of azabenzonorbornadienes with 2-arylindole,which does not require oxidants,and the reaction is featured by high regioselectivity and stereoselectivity with good functional group compatibility.The reaction yield is up to 98%under mild condition,and thus provides an efficient and convenient method for the synthesis of 2-aryl hydrogenaphthalene derivatives.

关 键 词：氮杂苯并冰片烯 吲哚 氢化萘 官能团化 C–H活化 

分 类 号：O621.251[理学—有机化学]