456-21-3Relevant articles and documents
Rapid and column-free syntheses of acyl fluorides and peptides usingex situgenerated thionyl fluoride
Lee, Cayo,Sammis, Glenn M.,Thomson, Brodie J.
, p. 188 - 194 (2021/12/31)
Thionyl fluoride (SOF2) was first isolated in 1896, but there have been less than 10 subsequent reports of its use as a reagent for organic synthesis. This is partly due to a lack of facile, lab-scale methods for its generation. Herein we report a novel protocol for theex situgeneration of SOF2and subsequent demonstration of its ability to access both aliphatic and aromatic acyl fluorides in 55-98% isolated yields under mild conditions and short reaction times. We further demonstrate its aptitude in amino acid couplings, with a one-pot, column-free strategy that affords the corresponding dipeptides in 65-97% isolated yields with minimal to no epimerization. The broad scope allows for a wide range of protecting groups and both natural and unnatural amino acids. Finally, we demonstrated that this new method can be used in sequential liquid phase peptide synthesis (LPPS) to afford tri-, tetra-, penta-, and decapeptides in 14-88% yields without the need for column chromatography. We also demonstrated that this new method is amenable to solid phase peptide synthesis (SPPS), affording di- and pentapeptides in 80-98% yields.
Acyl fluorides from carboxylic acids, aldehydes, or alcohols under oxidative fluorination
Liang, Yumeng,Zhao, Zhengyu,Taya, Akihito,Shibata, Norio
supporting information, p. 847 - 852 (2021/02/06)
We describe a novel reagent system to obtain acyl fluorides directly from three different functional group precursors: carboxylic acids, aldehydes, or alcohols. The transformation is achieved via a combination of trichloroisocyanuric acid and cesium fluoride, which facilitates the synthesis of various acyl fluorides in high yield (up to 99%). It can be applied to the late-stage functionalization of natural products and drug molecules that contain a carboxylic acid, an aldehyde, or an alcohol group.
Deoxyfluorination of Carboxylic Acids with KF and Highly Electron-Deficient Fluoroarenes
Mao, Siyu,Kramer, Jordan H.,Sun, Haoran
, p. 6066 - 6074 (2021/05/29)
A deoxyfluorination reaction of carboxylic acids using potassium fluoride (KF) and highly electron-deficient fluoroarenes is reported here, giving acyl fluorides in moderate to excellent yield (57-92% based on NMR integration and 34-95% for isolated examples).