Tappin Nicholas D C, Michalska Weronika, Rohrbach Simon, Renaud Philippe
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012, Bern, Switzerland.
Angew Chem Int Ed Engl. 2019 Oct 1;58(40):14240-14244. doi: 10.1002/anie.201907962. Epub 2019 Aug 23.
An operationally simple method to affect an atom-transfer radical addition of commercially available ICH Bpin to terminal alkenes has been developed. The intermediate iodide can be transformed in a one-pot process into the corresponding cyclopropane upon treatment with a fluoride source. This method is highly selective for the cyclopropanation of unactivated terminal alkenes over non-terminal alkenes and electron-deficient alkenes. Due to the mildness of the procedure, a wide range of functional groups such as esters, amides, alcohols, ketones, and vinylic cyclopropanes are well tolerated.
已开发出一种操作简单的方法，可实现市售的ICH Bpin与末端烯烃的原子转移自由基加成反应。在用氟源处理后，中间体碘化物可在一锅法中转化为相应的环丙烷。该方法对未活化的末端烯烃的环丙烷化反应具有高度选择性，优于非末端烯烃和缺电子烯烃。由于该方法的温和性，酯、酰胺、醇、酮和乙烯基环丙烷等多种官能团都能很好地耐受。
