Construction of Functionalized Azapolycyclic Architectures via Formal Amide Insertion at a Low Catalyst Loading of Copper Trifluoroacetylacetonate. Issue 19 (31st August 2016)

• Record Type: Journal Article
• Authors: Harada, Shingo; Kato, Ryosuke; Nemoto, Tetsuhiro
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 19(2016)
• Page Start: 3123
• Page End: 3129
• Publication Date: 2016-08-31
• Subjects: amides -- carbenoids -- copper -- diazo compounds -- insertion -- polycycles; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600603
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :