Journal
ORGANIC LETTERS
Volume 21, Issue 11, Pages 3998-4002Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01178
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Funding
- National Research Foundation of Korea (NRF) - Korean government [NRF-2016R1A2B4015351, NRF-2019R1A4A2001440]
- GRRC program of Gyeonggi Province [GRRCKyungHee2017-A01]
- Institute for Basic Science in Korea [IBS-R10-A1]
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A palladium-catalyzed reaction of N-aromatic zwitterion and trimethylenemethane that gives fused N-heterocycles via dearomative [3 + 2] cycloaddition and intramolecular cyclization is developed, and a cyclopentane-fused cyclic product is generated. Combining computational and experimental studies, the site-selective dearomatization and the mechanism of this novel reaction are investigated in detail, and the value of pyridinium zwitterion as a reactant is demonstrated.
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