Li Mingqiang, Zeng Weidi, Abdukader Ablimit, Wu Shaofeng, Zhou Lei
State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830046, Xinjiang, P. R. China.
Institute of Green Chemistry and Molecular Engineering, School of Chemistry, SunYat-Sen University, Guangzhou, 510275, China.
Org Lett. 2024 Sep 6;26(35):7452-7456. doi: 10.1021/acs.orglett.4c02788. Epub 2024 Aug 26.
A base-mediated regioselective [3 + 3] annulation of alkylidene malononitriles with trifluoromethyl alkenes was described. The reaction proceeds through sequential intermolecular S2' and intramolecular SV-type cyclization by cleaving dual C-F bonds in a trifluoromethyl group, which discriminate multiple carbon-nucleophilic sites using a single base. Various bicycles bearing a monofluorocyclohexene motif were assembled from readily available starting materials under mild conditions via a one-pot cascade approach.
描述了一种碱介导的亚烷基丙二腈与三氟甲基烯烃的区域选择性[3 + 3]环化反应。该反应通过分子间S2'反应和分子内SV型环化依次进行，通过裂解三氟甲基中的两个C-F键，使用单一碱区分多个碳亲核位点。在温和条件下，通过一锅串联法从易得的起始原料组装了各种带有单氟环己烯基序的双环化合物。
