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Construction of Functionalized Azapolycyclic Architectures via Formal Amide Insertion at a Low Catalyst Loading of Copper Trifluoroacetylacetonate
Author(s) -
Harada Shingo,
Kato Ryosuke,
Nemoto Tetsuhiro
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600603
Subject(s) - nonane , chemistry , amide , catalysis , copper , octane , ring (chemistry) , rhodium , formal synthesis , combinatorial chemistry , organic chemistry , polymer chemistry
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.