455-32-3Relevant articles and documents
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Wosnesenskii
, (1940)
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Proton Sponge Hydrofluoride as a Soluble Fluoride Ion Source
Chambers, Richard D.,Holmes, Thomas F.,Korn, Stewart R.,Standford, Graham
, p. 855 - 856 (1993)
Proton Sponge (PS) hydrofluoride has been prepared and is totally soluble in acetonitrile; this system was used to generate carbanions from hexafluoropropene and to form carbon-fluorine bonds by reaction with 2,4,6-trichloropyrimidine and by reaction with benzoyl chloride (Proton Sponge hydrochloride is insoluble in acetonitrile).
Olah et al.
, p. 6717 (1976)
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 CpFluor: Access to Acyl Fluorides and Amides
Wang, Xiu,Wang, Fei,Huang, Fengfeng,Ni, Chuanfa,Hu, Jinbo
supporting information, p. 1764 - 1768 (2021/03/03)
3,3-Difluoro-1,2-diphenylcyclopropene (CpFluor), a bench-stable fluorination reagent, has been developed in the deoxyfluorination of carboxylic acids to afford various acyl fluorides. This all-carbon-based fluorination reagent enabled the efficient transformation of (hetero)aryl, alkyl, alkenyl, and alkynyl carboxylic acids to the corresponding acyl fluorides under the neutral conditions. This deoxyfluorination method was featured by the synthesis of acyl fluorides with in-situ formed CpFluor, as well as the one-pot amidation reaction of carboxylic acids via in-situ formed acyl fluorides.
Direct amidation of acid fluorides using germanium amides
Hayatifar, Ardalan,Elifritz, Emily A.,Bloom, Molly B.,Pixley, Kaitlyn M.,Fennell, Christopher J.,Weinert, Charles S.
supporting information, p. 4490 - 4493 (2021/04/12)
Amide functional groups are an essential linkage that are found in peptides, proteins, and pharmaceuticals and new methods are constantly being sought for their formation. Here, a new method for their preparation is presented where germanium amides Ph3GeNR2convert acid fluorides directly to amides. These germanium amides serve to abstract the fluorine atom of the acid fluoride and transfer their amide group -NR2to the carbonyl carbon, and so function as amidation reagents.