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通过C-H活化实现导向基团控制的氧杂/氮杂苯并降冰片二烯与芳烃的开环加成及氢芳基化反应

Directing-Group-Controlled Ring-Opening Addition and Hydroarylation of Oxa/azabenzonorbornadienes with Arenes via C-H Activation.

作者信息

Zhang Keyang, Khan Ruhima, Chen Jingchao, Zhang Xuexin, Gao Yang, Zhou Yongyun, Li Kangkui, Tian Youxian, Fan Baomin

机构信息

Key Laboratory of Chemistry in Ethnic Medicinal Resources, Yunnan Minzu University, Kunming 650500, China.

School of Chemistry and Environment, Institution Yunnan Minzu University, Yuehua Street, Kunming, 650500, China.

出版信息

Org Lett. 2020 May 1;22(9):3339-3344. doi: 10.1021/acs.orglett.0c00765. Epub 2020 Apr 17.

Abstract

An efficient method for the directing group controlled rhodium-catalyzed addition reaction of oxa/azabicylic alkenes with aromatic ketones and benzoic acids has been developed. The ketones and benzoic acids afforded different addition products when reacted with oxa/azabicyclic alkenes. The reaction between ketones and azabenzonorbornadienes furnished the ring-opening addition products. The reaction between benzoic acids and aza/oxabicyclic alkenes proceeded in the absence of silver salt, giving the 1:2 hydroarylation products in yields up to 96%.

摘要

已开发出一种有效的方法,用于导向基团控制的铑催化的氧杂/氮杂双环烯烃与芳香酮和苯甲酸的加成反应。酮和苯甲酸与氧杂/氮杂双环烯烃反应时会生成不同的加成产物。酮与氮杂苯并降冰片二烯之间的反应得到开环加成产物。苯甲酸与氮杂/氧杂双环烯烃之间的反应在无银盐的情况下进行,以高达96%的产率得到1:2的氢芳基化产物。

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