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Widely Applicable Hydrofluorination of Alkenes via Bifunctional Activation of Hydrogen Fluoride

Zhichao Lu, Xiaojun Zeng, Gerald B. Hammond* and Bo Xu*

*University of Louisville, Louisville, Kentucky 40292, United States; Donghua University, 2999 North Renmin Lu, Shanghai 201620, China, Email: gb.hammondlouisville.edu, bo.xudhu.edu.cn

Z. Lu, X. Zeng, G. B. Hammon, B. Xu, J. Am. Chem. Soc., 2017, 139, 18202-18205.

DOI: 10.1021/jacs.7b12704


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Abstract

KHSO4-13HF (HF 68 wt/wt-%) as is an easily handled and inexpensive nucleophilic fluorination reagent, that is capable of hydrofluorinating diverse, highly functionalized alkenes, including natural products. The high efficiency of this reaction is caused by the activation of HF with a highly "acidic" hydrogen bond acceptor.

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Bifunctional Activation Strategy for Hydrofluorination of Alkenes



Key Words

alkyl fluorides


ID: J48-Y2017