Theoretical study of Lewis acid activation models for hypervalent fluoroiodane reagent: The generality of "F-coordination" activation model. Issue 13 (29th March 2017)

• Record Type: Journal Article
• Authors: Zhou, Biying; Xue, Xiao-song; Cheng, Jin-pei
• Is Part Of: Tetrahedron letters. Volume 58:Issue 13(2017)
• Page Start: 1287
• Page End: 1291
• Publication Date: 2017-03-29
• Subjects: Hypervalent fluoroiodane reagent -- Fluorination -- Lewis acid activation -- F-coordination model -- DFT calculations; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.02.040
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: F-coordination is favored over O-coordination activation model for fluoroiodane. Brønsted acid can work synergistically with Lewis acid to activate fluoroiodane. Calculations demonstrate the generality of F-coordination activation mechanism for fluoroiodane. Abstract: The bench-stable cyclic hypervalent fluoroiodane reagent (1 ) is receiving increasing attention in fluorine chemistry because of its completely new reactivity. Fluorination mediated by reagent1 generally requires activation by an exogenous Lewis acid. A more complete understanding of the Lewis acid activation model is thus paramount for the development of new strategies involving this reagent. Density functional theory (DFT) calculations herein demonstrate the generality of the "F-coordination" activation mechanism for reagent1 that we recently showed to be favored over the commonly accepted "O-coordination" activation mechanism.