Exploring the Versatility of the Amidation of Aryl Acid Fluorides using the Germylamines R 3 GeNMe 2

• Published in: Chemistry, an Asian journal an Asian journal, 2023-12, Vol.18 (24), p.e202300788
• Main Authors: Fortney, Vanessa A, Murphy, Julia K, Stancil, Thad R, Gembicky, Milan, Rheingold, Arnold L, Weinert, Charles S
• Format: Article
• Language: English
• ISSN: 1861-4728; 1861-471X
• DOI: 10.1002/asia.202300788

The formation of amide bonds is an important process since this linkage is an essential component in proteins, pharmaceuticals, and other medicinally and biologically significant molecules. Recently, it was demonstrated that germylamines R GeNR' were useful reagents for the conversion of acid fluorides to amides. This transformation occurs readily at room temperature and has a low activation energy. In the present study, the versatility of this amidation reaction with aryl acid fluorides is investigated. A series of thirteen acid fluorides with various substituents on the aromatic ring were reacted with the germylamine Ph GeNMe and twelve of these were converted to the corresponding amides in high yields, the exception being 1,4-benzenedicarbonyl difluoride. The germylamines Bu GeNMe and Pr GeNMe also could be used for this interconversion, and both of these species successfully converted 1,4-benzenedicarbonyl difluoride to the corresponding amide. In addition, the crystal structure of Ph GeNMe is reported. This represents one of only three crystallographically characterized germylamines. The synthesis and F NMR characterization of three fluorogermanes R GeF (R=Bu , Pr , and Mes) are also reported herein.