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Widely Applicable Hydrofluorination of Alkenes via Bifunctional Activation of Hydrogen Fluoride.

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.

SUBMITTER: Lu Z

PROVIDER: S-EPMC5742534 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Widely Applicable Hydrofluorination of Alkenes via Bifunctional Activation of Hydrogen Fluoride.

Lu Zhichao Z Zeng Xiaojun X Hammond Gerald B GB Xu Bo B

Journal of the American Chemical Society 20171212 50

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, KHSO<sub>4</sub>-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 t ...[more]

PMID: 29206450

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