106468-03-5Relevant academic research and scientific papers
Convenient fluorination of nitro and nitrile compounds with Selectfluor
Peng, Weimin,Shreeve, Jean'ne M.
, p. 4905 - 4909 (2007/10/03)
A variety of nitro and nitrile compounds were fluorinated in good yields by Selectfluor under mild conditions. For these transformations to be successful, it is crucial to select proper amounts of an appropriate base as a function of the properties of the substrate and also to use Selectfluor only as required.
Enantioselective hydrolysis of (RS)-2-fluoroarylacetonitriles using nitrilase from Arabidopsis thaliana
Effenberger, Franz,Osswald, Steffen
, p. 279 - 285 (2007/10/03)
The enzymatic resolution of 2-fluoroarylacetonitriles (RS)-3 using nitrilase from the plant Arabidopsis thaliana is described. Racemic 2-fluoronitriles 3 are easily accessible from O-silylated aromatic cyanohydrins 2 by reaction with DAST. The nitriles (RS)-3 were hydrolysed with the nitrilase as a catalyst, not to the expected 2-fluoroarylacetic acids but to the corresponding (R)-2-fluoroarylacetamides (R)-5 as the main products. After optimization of reaction conditions (pH 9, 7°C), the enantiomeric excesses of (R)-5a,c and f (R=H, 3-Me, 3-OMe) could be improved to >99% by one recrystallization. The acid catalysed hydrolysis of (R)-5a,5c and 5f afforded the corresponding (R)-2-fluoroarylacetic acids (R)-4a,4c and 4f without racemization.
