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Stereodivergent Alkyne Hydrofluorination Using a Simple Practical Reagent

revised on 21.03.2020, 03:05 and posted on 23.03.2020, 09:42 by Rui Guo, Xiaotian Qi, Hengye Xiang, Paul Geaneoates, Ruihan Wang, Peng Liu, Yiming Wang
Vinyl fluorides play an important role in drug development as they serve as bioisosteres for peptide bonds and are found in a range of biologically active molecules. The discovery of safe, general and practical procedures to prepare vinyl fluorides remains an important goal and challenge for synthetic chemistry. Here we introduce an inexpensive and easily-handled reagent and report simple, scalable, and metal-free protocols for the regioselective and stereodivergent hydrofluorination of alkynes to access both the E and Z isomers of vinyl fluorides. These conditions were suitable for a diverse collection of alkynes, including several highly-functionalized pharmaceutical derivatives. Mechanistic and DFT studies support C–F bond formation through a vinyl cation intermediate, with the (E)- and (Z)-hydrofluorination products forming under kinetic and thermodynamic control, respectively.


Computational Models for Reactivity and Selectivity in Transition Metal-Catalyzed Olefin Functionalization

National Institute of General Medical Sciences

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University of Pittsburgh



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Declaration of Conflict of Interest

The authors declare no competing interests.

Version Notes

Corrected important error in figure 1 of manuscript and updated the supporting information.


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in Angewandte Chemie International Edition