Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 19, Pages 3123-3129Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600603
Keywords
amides; carbenoids; copper; diazo compounds; insertion; polycycles
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Funding
- JSPS [JP26860008, JP16K18840]
- Grants-in-Aid for Scientific Research [16K18840] Funding Source: KAKEN
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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.
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