Construction of Functionalized Azapolycyclic Architectures via Formal Amide Insertion at a Low Catalyst Loading of Copper Trifluoroacetylacetonate

Construction of Functionalized Azapolycyclic Architectures via Formal Amide Insertion at a Low Catalyst Loading of Copper Trifluoroacetylacetonate
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在三氟乙酰丙酮铜的低催化剂负载量下通过形式酰胺插入构建功能化氮杂多环结构

DOI:
10.1002/adsc.201600603
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发表时间:
2016
影响因子:
5.4
通讯作者:
Tetsuhiro Nemoto
Tetsuhiro Nemoto
中科院分区:
化学2区
文献类型:
--
作者:
Shingo Harada;Ryosuke Kato;Tetsuhiro Nemoto

文献摘要

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使用可持续的铜催化剂作为贵重铑催化剂的有利替代品,开发了一种用于合成具有多种功能的氮桥多环骨架的正式酰胺插入反应。该方法的显着特点是催化剂负载量(0.05 mol%)。优化的反应条件能够以中等至优异的产率获得芳香环稠合的8-氮杂双环[3.2.1]辛烷、9-氮杂双环[3.3.1]壬烷和6-氮杂双环[3.2.2]壬烷衍生物。
A formal amide insertion reaction for the synthesis of nitrogen‐bridged polycyclic frameworks with diverse functionalities was developed using a sustainable copper catalyst as an advantageous alternative to precious rhodium catalysts. The remarkable feature of this methodology is the amount of catalyst loading (0.05 mol%). The optimized reaction conditions enable access to aromatic ring‐fused 8‐azabicyclo[3.2.1]octane, 9‐azabicyclo[3.3.1]nonane, and 6‐azabicyclo[3.2.2]nonane derivatives in moderate to excellent yields.