Organic Letters
Organic Letters
5 years ago

Radical Silyldifluoromethylation of Electron-Deficient Alkenes

Radical Silyldifluoromethylation of Electron-Deficient Alkenes
Alexander D. Dilman, Vyacheslav I. Supranovich, Marina I. Struchkova, Vitalij V. Levin, Alexander A. Korlyukov
A reaction of bromo- and iododifluoromethyl-substituted silanes with electron-deficient alkenes in the presence of an N-heterocyclic carbene borane complex is described. The reaction is performed under irradiation with light-emitting diodes and proceeds via a radical chain mechanism. The resulting products, the functionalized silicon reagents, can undergo chemoselective transformations involving either the silyldifluoromethyl fragment or the functional group.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01334

DOI: 10.1021/acs.orglett.7b01334

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