Electrochemical alkene azidocyanation <i>via</i> 1,4-nitrile migration
Alex C. Seastram, Mishra Deepak Hareram, Thomas M. B. Knight, Louis C. Morrill
Abstract
1,4-nitrile migration has been developed. This organic oxidant free method is applicable across various alkene containing cyanohydrins, and provides access to a broad range of synthetically useful 1,2-azidonitriles (28 examples). This methodology was extended to an electrochemical alkene sulfonylcyanation procedure, as well as to access a trifunctionalized hexanenitrile from a malononitrile starting material. The orthogonal derivatization of the products was also demonstrated through chemoselective transformations.
Topics & Concepts
AlkeneNitrileMalononitrileElectrochemistryDerivatizationChemistryCombinatorial chemistryOrganic chemistryElectrodeCatalysisHigh-performance liquid chromatographyPhysical chemistryRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods