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. 2014 Oct 15;136(41):14381-4.
doi: 10.1021/ja508369z. Epub 2014 Oct 2.

Designer HF-based fluorination reagent: highly regioselective synthesis of fluoroalkenes and gem-difluoromethylene compounds from alkynes

Otome E Okoromoba  1 , Junbin Han, Gerald B Hammond, Bo Xu
Affiliations

Designer HF-based fluorination reagent: highly regioselective synthesis of fluoroalkenes and gem-difluoromethylene compounds from alkynes

Otome E Okoromoba et al. J Am Chem Soc. .

Abstract

Hydrogen fluoride (HF) and selected nonbasic and weakly coordinating (toward cationic metal) hydrogen-bond acceptors (e.g., DMPU) can form stable complexes through hydrogen bonding. The DMPU/HF complex is a new nucleophilic fluorination reagent that has high acidity and is compatible with cationic metal catalysts. The gold-catalyzed mono- and dihydrofluorination of alkynes using the DMPU/HF complex yields synthetically important fluoroalkenes and gem-difluoromethlylene compounds regioselectively.

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Figures

Figure 1
Figure 1
Comparison of DMPU/HF with pyridine/HF and Et3N/HF.
Scheme 1
Scheme 1. Selectivity of the DMPU/HF/Au-1 Fluorination System
Scheme 2
Scheme 2. Synthesis of Fluorocarbocycles
See this image and copyright information in PMC

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