Electrochemical Cyclopropanation of Unactivated Alkenes with Methylene Compounds
Min Liu
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorYanwei Wang
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorChao Gao
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorJingpei Jia
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorZile Zhu
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Youai Qiu
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorMin Liu
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorYanwei Wang
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorChao Gao
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorJingpei Jia
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorZile Zhu
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Youai Qiu
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorAbstract
Cyclopropanes are prevalent in natural products, pharmaceuticals, and bioactive compounds, functioning as a significant structural motif. Although a series of methods have been developed for the construction of the cyclopropane skeleton, the development of a direct and efficient strategy for the rapid synthesis of cyclopropanes from bench-stable starting materials with a broad substrate scope and functional group tolerance remains challenging and highly desirable. Herein, we present an electrochemical method for the direct cyclopropanation of unactivated alkenes using active methylene compounds. The strategy shows a broad substrate scope with a high level of functional group compatibility, as well as potential application as demonstrated by late-stage cyclopropanation of complex molecules and drug derivatives. Further mechanistic investigations suggest that Cp2Fe (Fc) plays an essential role as an oxidative mediator in generating radicals from active methylene compounds.
Open Research
Data Availability Statement
Materials and methods, optimization studies, experimental procedures, mechanistic studies, 1H NMR, 13C NMR and 19F NMR spectra, and high-resolution mass spectrometry data are available in the Supporting Information. Deposition Number 2402258 (for 49) contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
Supporting Information
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