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Widely Applicable Hydrofluorination of Alkenes via Bifunctional Activation of Hydrogen Fluoride

[Image: see text] 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(4)-13HF, HF 68 wt/wt %, th...

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Detalles Bibliográficos
Autores principales: Lu, Zhichao, Zeng, Xiaojun, Hammond, Gerald B., Xu, Bo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5742534/
https://www.ncbi.nlm.nih.gov/pubmed/29206450
http://dx.doi.org/10.1021/jacs.7b12704
Descripción
Sumario:[Image: see text] 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(4)-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.