1,4-Fluoroamination of 1,3-Enynes en Route to Fluorinated Allenes
Qi Zhang, Munira Taj Muhammad, Mong‐Feng Chiou, Yihang Jiao, Hongli Bao, Yajun Li
Abstract
The regioselective synthesis of fluorinated allenes via a metal-free 1,4-fluoroamination of 1,3-enynes is presented. This method employs commercially available N-fluorobenzenesulfonimide serving as both the nitrogen source and the fluorine source, affording access to various tetrasubstituted allenes in a straightforward and atom-economic pathway. Preliminary mechanistic studies and theoretical studies revealed that this reaction might undergo an intimate ion-pair mechanism.
Topics & Concepts
ChemistryRegioselectivityNitrogen atomFluorineCombinatorial chemistryCatalysisOrganic chemistryRing (chemistry)Fluorine in Organic ChemistryCatalytic C–H Functionalization MethodsInorganic Fluorides and Related Compounds