1978-21-8Relevant articles and documents
Synthesis of Acyl Fluorides from Carboxylic Acids Using NaF-Assisted Deoxofluorination with XtalFluor-E
Gonay, Marie,Batisse, Chloé,Paquin, Jean-Fran?ois
, p. 10253 - 10260 (2020/08/12)
The synthesis of acyl fluorides using the deoxofluorination reaction of carboxylic acids using XtalFluor-E is described. This transformation, assisted by a catalytic amount of NaF, occurs at room temperature in EtOAc, where XtalFluor-E behaves as the activating agent and the fluoride source. A wide range of acyl fluorides were obtained in moderate to excellent yields (36-99%) after a simple filtration on a pad of silica gel. We also demonstrated that sequential deoxofluorination/amidation was possible.
Liquid-phase synthesis of 2-substituted benzimidazoles, benzoxazoles and benzothiazoles
Chen, Chinpiao,Chen, Yi-Jing
, p. 113 - 115 (2007/10/03)
A novel acid fluoride for use in the liquid-phase synthesis of substituted benzimidazoles, benzoxazoles and benzothiazoles was developed. Its synthetic utility is exemplified by a structurally diverse set of aromatic heterocycles. Final cleavage is achiev
Catalytic Acid Fluoride Synthesis via Carbonylation of Organic Bromides in the Presence Potassium Fluoride
Okano, Tamon,Harada, Nobuyuki,Kiji, Jitsuo
, p. 1741 - 1743 (2007/10/02)
Various aryl bromides were carbonylated under an atmospheric pressure of carbon monoxide in DMF in the presence of potassium fluoride to give aroyl fluorides in excellent yields.The carbonylation was promoted by the addition of phase transfer catalysts, but the contamination with water reduced the selectivity.
The Relationship between 19F Substituent Chemical Shifts and Electron Densities: meta- and para-Substituted Benzoyl Fluorides
Brownlee, Robert T. C.,Craik, David J.
, p. 186 - 191 (2007/10/02)
The 19F substituent chemical shifts (SCS) of meta- and para-benzoyl fluorides are found to correlate well with substituent parameters using the dual substituent parameter (DSP) equation, indicating that they reflect electronic perturbations induced by the substituent.The direction of the SCS values is such that donating substituents cause upfield shifts whilst acceptors cause downfield shifts.STO-3G calculations indicate that substituents induce only very small changes in ?-electron density about the fluorine atom, but that these changes correlate reasonably well with the observed SCS values.For the para series, the slope of the relationship between Δq?F and 19F SCS is 5000 ppm/electron, indicating the great sensitivity of the fluorine atom to small changes in electron density.
