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. 2017 Dec 20;139(50):18202-18205.
doi: 10.1021/jacs.7b12704. Epub 2017 Dec 12.

Widely Applicable Hydrofluorination of Alkenes via Bifunctional Activation of Hydrogen Fluoride

Zhichao Lu  1 , Xiaojun Zeng  2 , Gerald B Hammond  1 , Bo Xu  2
Affiliations

Widely Applicable Hydrofluorination of Alkenes via Bifunctional Activation of Hydrogen Fluoride

Zhichao Lu et al. J Am Chem Soc. .

Abstract

Expanding the use of fluorine in pharmaceuticals, agrochemicals and materials requires a widely applicable and more efficient protocol for the preparation of fluorinated compounds. We have developed a new generation nucleophilic fluorination reagent, KHSO4-13HF, HF 68 wt/wt %, that is not only easily handled and inexpensive but also capable of hydrofluorinating diverse, highly functionalized alkenes, including natural products. The high efficiency observed in this reaction hinges on the activation of HF using a highly "acidic" hydrogen bond acceptor.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Strategies for the Hydrofluorination of Alkenes
Scheme 2
Scheme 2. Bifunctional Activation Strategy for Hydrofluorination of Alkenes
See this image and copyright information in PMC

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