Kinetically Controlled Radical Addition/Elimination Cascade: From Alkynyl Aziridine to Fluorinated Allenes
Tingting Song, Lei Zhu, Haoyu Li, Chen‐Ho Tung, Yu Lan, Zhenghu Xu
Abstract
A kinetically controlled radical addition/elimination reaction generating fluorinated allenes was developed. This strategy offers a route to a facile synthesis of diverse trifluoromethyl, difluoromethylene, and perfluoroalkyl functionalized allenes from readily available fluoroalkyl halides and alkynyl aziridines under visible-light irradiation. Density functional theory calculation of this radical clock type of reaction revealed a kinetically controlled C-N bond cleavage overcoming the alternative thermodynamically controlled C-C bond cleavage process.
Topics & Concepts
ChemistryAziridineCascadeAlleneCascade reactionCombinatorial chemistryMedicinal chemistryOrganic chemistryPhotochemistryCatalysisRing (chemistry)ChromatographyFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods