Department of Polymer Science and Engineering, School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of Microstructures, Nanjing University , Nanjing 210093, China.
Org Lett. 2016 Aug 5;18(15):3806-9. doi: 10.1021/acs.orglett.6b01805. Epub 2016 Jul 19.
A Co(III)-catalyzed, internal and terminal alkyne-compatible indole synthesis protocol is reported herein. The N-amino (hydrazine) group imparts distinct, diverse reactivity patterns for directed C-H functionalization/cyclization reactions. Notable synthetic features include regioselectivity for a meta-substituted arylhydrazine, regioselectivity for a chain-branched terminal alkyne, formal incorporation of an acetylenic unit through C2-desilylation on a C2-silylated indole derivative, formal inversion of regioselectivity through consecutive C3-derivatization and C2-desilylation processes, and formal bond migration for a linear-chain terminal alkyne.
本文报道了一种 Co(III)-催化、内部和末端炔兼容的吲哚合成方法。N-氨基（肼）基团为导向 C-H 功能化/环化反应赋予了独特的、多样化的反应性模式。显著的合成特点包括对间位取代芳基腙的区域选择性、对支链末端炔的区域选择性、通过 C2-脱硅烷基化在 C2-硅基化吲哚衍生物上正式引入炔基单元、通过连续的 C3-衍生化和 C2-脱硅烷基化过程实现区域选择性的反转以及线性链末端炔的形式键迁移。
