Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents
| العنوان: | Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents |
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| المؤلفون: | Yi-Ming Wang, Paul Geaneotes, Peng Liu, Hengye Xiang, Ruihan Wang, Xiaotian Qi, Rui Guo |
| المصدر: | Angew Chem Int Ed Engl |
| بيانات النشر: | Wiley, 2020. |
| سنة النشر: | 2020 |
| مصطلحات موضوعية: | Reaction mechanism, Vinyl Compounds, Halogenation, Alkyne, 010402 general chemistry, 01 natural sciences, Article, Catalysis, chemistry.chemical_compound, Borates, Vinyl fluoride, chemistry.chemical_classification, Reaction conditions, Molecular Structure, 010405 organic chemistry, Regioselectivity, Stereoisomerism, General Chemistry, General Medicine, Bond formation, Combinatorial chemistry, 0104 chemical sciences, chemistry, Alkynes, Reagent, Vinyl cation |
| الوصف: | Vinyl fluorides play an important role in drug development as bioisosteres for peptide bonds and are found in a range of bioactive molecules. The discovery of safe, general and practical procedures to prepare vinyl fluorides from readily available precursors remains a synthetic challenge. The metal-free hydrofluorination of alkynes constitutes an attractive though elusive strategy for their preparation. Here we introduce an inexpensive and easily-handled reagent that enabled the development of simple and scalable protocols for the regioselective 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. Computational and experimental mechanistic studies support C–F bond formation through vinyl cation intermediates, with the (E)- and (Z)-hydrofluorination products forming under kinetic and thermodynamic control, respectively. |
| تدمد: | 1521-3757 0044-8249 |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::38293b41b64b1636cbf7e2b95a3fef56Test https://doi.org/10.1002/ange.202006278Test |
| حقوق: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....38293b41b64b1636cbf7e2b95a3fef56 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15213757 00448249 |
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