ol9b01178_si_001.pdf (3.9 MB)
Catalytic Cascade Reaction To Access Cyclopentane-Fused Heterocycles: Expansion of Pd–TMM Cycloaddition
journal contribution
posted on 2019-05-15, 00:00 authored by Donguk Ko, Seung-yeol Baek, Jae Yul Shim, Ju Young Lee, Mu-Hyun Baik, Eun Jeong YooA 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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mechanismPdcycloadditionreactantsite-selective dearomatizationN-heterocycledearomativetrimethylenemethaneCatalytic Cascade Reactionintramolecular cyclizationN-aromatic zwitterionpalladium-catalyzed reactioncyclopentane-fused cyclic productpyridinium zwitterionAccess Cyclopentane-Fused Heterocyclesnovel reactionCycloaddition
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