Dual Photoredox/Copper Catalyzed Fluoroalkylative Alkene Difunctionalization
Vladislav S. Kostromitin, Vitalij V. Levin, Alexander D. Dilman
Abstract
A method for performing radical difunctionalization of alkenes using fluorinated halides and a nucleophilic component (thiolate and iodide anions) is described. These nucleophilic fragments serve as redox active groups for performing subsequent transformations. The difunctionalization reaction involves photoredox generation of fluorinated radicals, their addition to the double bond followed by copper-promoted C-S or C-I bond formation. The primary products can be further coupled with silyl enol ethers, α-(trifluoromethyl)styrenes, and trimethylsilyl cyanide affording a variety of fluorinated compounds.
Topics & Concepts
ChemistryNucleophileEnolAlkeneTrimethylsilyl cyanideIodideRadicalPhotoredox catalysisSilylationPhotochemistryTrifluoromethylCatalysisDouble bondCyanideCopperOrganic chemistryPhotocatalysisAlkylFluorine in Organic ChemistryRadical Photochemical ReactionsSulfur-Based Synthesis Techniques