Activation of the hypervalent fluoroiodane reagent by hydrogen bonding to hexafluoroisopropanol?

Organic & Biomolecular Chemistry Pub Date: 2018-09-18 DOI: 10.1039/C8OB02236D

Abstract

Hexafluoroisopropan-2-ol (HFIP) is an excellent solvent for promoting fluorinations with the hypervalent fluoroiodane reagent 1 and crucially, it removes the need for transition metals or TREAT-HF activators. The fluoroiodane reagent 1 was used in HFIP to monofluorinate 1,3-ketoesters and to fluorocyclise unsaturated carboxylic acids in excellent yields under mild reaction conditions.

Graphical abstract: Activation of the hypervalent fluoroiodane reagent by hydrogen bonding to hexafluoroisopropanol
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