Li Linxuan, Chen Hongzhu, Zhang Xiaolong, Murali Karunanidhi, Zhu Qingwen, Liu Menglin, Zhang Hongru, Nenajdenko Valentine, Bi Xihe
Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Department of Chemistry, Lomonosov Moscow State University, 119899 Moscow, Russia.
Org Lett. 2024 Aug 30;26(34):7207-7211. doi: 10.1021/acs.orglett.4c02633. Epub 2024 Aug 15.
Here, we report a silver carbene-enabled single-carbon insertion reaction of indoles via a one-pot, two-step sequence to deliver a dearomative quaternary center quinoline scaffold in a modular fashion. Specifically, we used -triftosylhydrazones as masked donor-donor carbene precursors that facilitate the insertion of carbon atoms bearing various functional groups to the library of functionalized quinoline. Experimental and DFT evidence support the transient presence of a cyclopropane species and removal of protecting groups.
在此，我们报道了一种通过一锅两步序列实现的、由银卡宾介导的吲哚单碳插入反应，该反应以模块化方式构建了一个去芳构化的季碳中心喹啉骨架。具体而言，我们使用α-三氟甲磺酰腙作为掩蔽的供体-供体卡宾前体，促进带有各种官能团的碳原子插入到功能化喹啉库中。实验和密度泛函理论证据支持环丙烷物种的瞬时存在以及保护基团的去除。
