Palladium-Catalyzed Aminomethylation and Cyclization of Enynol to O‑Heterocycle Confined 1,3-Dienes
journal contributionposted on 10.05.2021, 16:10 by Houjian Yu, Bangkui Yu, Haocheng Zhang, Hanmin Huang
The rational tuning of the electrophilicity of the allylpalladium intermediates enables the regioselectively intramolecular 1,2-addition of enynol in the presence of aminal. This aminomethylation and cyclization reaction via C–N bond activation and intramolecular nucleophilic addition provides a rare example for the synthesis of O-containing heterocycle-confined 1,3-dienes, which is of synthetic potential for further derivatization. The method possesses broad substrate generality as well as functional group compatibility and efficiently affords a wide range of desired products with 5-, 6-, and 8-membered O-containing heterocycles with various functional groups.
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allylpalladium intermediatesEnynol8- membered O-containing heterocyclesCyclizationcyclization reactionaminomethylationgroup compatibilityenynolpresenceheterocycle-confinedConfinedmethoddienesynthesisactivationsubstrate generalityregioselectivelyaminalderivatizationDieneintramolecular nucleophilic additionPalladium-Catalyzed Aminomethylationelectrophilicitybond