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Organocalcium Hydride-Catalyzed Intramolecular C(sp3)–H Annulation of Functionalized 2,6-Lutidines

Journal 2023 · IF 3.6 · 发表于 2023 年 1 月 16 日
作者: Shuo Li,Xian Xu,Qianlin Sun,Xin Xu
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摘要

This work reports an intramolecular C(sp3)–H annulation of functionalized 2,6-lutidines catalyzed by an organocalcium hydride [{(DIPPnacnac)CaH(thf)}2] (DIPPnacnac = CH{(CMe)(2,6-iPr2–C6H3N)}2). This reaction constitutes a streamlined approach for producing a new family of tetrahydro-1,5-naphthyridines and hexahydropyrido[3,2-b]azocines derivatives in good to excellent yields with high atom efficiency and broad substrates scope. A calcium alkyl complex was isolated from the stoichiometric reaction between calcium hydride and the substrate through deprotonation, which was structurally characterized and confirmed as the catalytic intermediate.