Journal
ORGANIC LETTERS
Volume 23, Issue 11, Pages 4256-4260Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01173
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Funding
- National Research Foundation of Korea (NRF) [NRF-2019R1A2C1087134, NRF-2019R1A4A2001440]
- Korean government
- GRRC program of Gyeonggi Province [GRRCKyungHee2017-A01]
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By carefully controlling the reaction kinetics and utilizing a silver catalyst, a catalytic ring expansion of activated heteroarenes was achieved through 1,4-dearomative addition to construct fused azepines. The developed methodology offers an innovative approach for the synthesis of biologically relevant multifused azepines, showcasing excellent substrate scope and selectivity.
Catalytic ring expansion of activated heteroarenes through 1,4-dearomative addition of diazoacetates was established for the construction of various fused azepines by an elaborate control of the reaction kinetics at each step. The use of a silver catalyst was essential to drive the overall reaction for generating the desired seven-membered azepines. Because of the excellent substrate scope and selectivity, the developed methodology presents an innovative approach for the synthesis of multifused azepines, which are biologically relevant molecules.
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