85371-03-5Relevant academic research and scientific papers
α-Bromo-α,α-difluoroallyl derivatives as synthetic intermediate: Nucleophilic substitution of α-bromo-α,α-difluoroallyl derivatives in the presence of palladium catalysts
Kirihara, Masayuki,Takuwa, Tomofumi,Okumura, Maiko,Wakikawa, Takahiro,Takahata, Hiroki,Momose, Takefumi,Takeuchi, Yoshio,Nemoto, Hideo
, p. 885 - 888 (2000)
The palladium catalyzed nucleophilic substitution of α-bromo-α, α- difluoroallyl derivatives turned out to be an efficient method for the preparation of several fluorinated organic molecules. Several soft carbon nucleophiles regioselectively reacted with
Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents
Geaneotes, Paul,Guo, Rui,Liu, Peng,Qi, Xiaotian,Wang, Ruihan,Wang, Yi-Ming,Xiang, Hengye
supporting information, p. 16651 - 16660 (2020/07/16)
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. Introduced here is an inexpensive and easily handled reagent that enables 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 reaction 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.
Preparation of fluoroalkenes via the Shapiro reaction: Direct access to fluorinated peptidomimetics
Yang, Ming-Hsiu,Matikonda, Siddharth S.,Altman, Ryan A.
supporting information, p. 3894 - 3897 (2013/09/02)
Fluoroalkenes represent a useful class of peptidomimetics with distinct biophysical properties. Current preparations of this functional group commonly provide mixtures of E- or Z-fluoroalkene diastereomers, and/or mixtures of nonfluorinated products. To directly access fluoroalkenes in good stereoselectivity, a Shapiro fluorination reaction was developed. Fluoroalkene products were accessed in one- or two-step sequences from widely available ketones. This strategy should be useful for the preparation of fluorinated analogs of peptide-based therapeutics, many of which would be challenging to prepare by alternate strategies.
