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Catalytic Cascade Reaction To Access Cyclopentane-Fused Heterocycles: Expansion of Pd–TMM Cycloaddition

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journal contribution
posted on 15.05.2019 by Donguk Ko, Seung-yeol Baek, Jae Yul Shim, Ju Young Lee, Mu-Hyun Baik, Eun Jeong Yoo
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.