Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes
Zhichao Lu, Olivia Hennis, Joseph Gentry, Bo Xu, Gerald B. Hammond
Abstract
The base-induced reaction of aryl diazonium salts with commercially available CF3SO2Na/CF2HSO2Na allows for the generation of the corresponding diazene radicals along with fluoromethyl radicals. The addition of fluoromethyl radicals to alkenes with subsequent diazene trapping provides the azofluoromethylation products in good to excellent yields. This metal-free method under mild reaction conditions has broad functional group compatibility and is applicable in the late-stage modification of various natural products and bioactive molecules.
Topics & Concepts
RadicalChemistryArylFunctional groupMoleculeCombinatorial chemistryBase (topology)Aryl radicalReaction conditionsPhotochemistryOrganic chemistryCatalysisAlkylMathematicsMathematical analysisPolymerFluorine in Organic Chemistry