194344-13-3Relevant academic research and scientific papers
Synthesis and Solid State 13C and 19F NMR Characterization of Aliphatic and Aromatic Carboxylic Acid Fluoride Polymers
Hagaman, Edward W.,Lee, Suk Kyu,Britt, Phillip F.
, p. 3950 - 3958 (1997)
A new chemical/spectroscopic couple that differentiates aromatic from aliphatic carboxylic acid polymers was developed. The method is complementary to more traditional methods of identification (IR) and is applicable to the analysis of complex mixtures wh
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).
METHOD AND REAGENT FOR DEOXYFLUORINATION
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Paragraph 0111-0112; 0114; 0127, (2021/05/29)
A safe, simple, and selective method and reagent for deoxyfluorination is disclosed. With the method and reagent disclosed herein, organic compounds such as carboxylic acids, carboxylates, carboxylic acid anhydrides, aldehydes, and alcohols can be fluorinated by using the most common nucleophilic fluorinating reagents and electron deficient fluoroarenes as mediators under mild conditions, giving corresponding fluoroorganic compounds in excellent yield with a wide range of functional group compatibility and easy product purification. For example, directly utilizing KF for deoxyfluorination of carboxylic acids provides the most economical and the safest pathway to access acyl fluorides, key intermediates for syntheses of peptide, amide, ester, and dry fluoride salts.
Direct Access to Acyl Fluorides from Carboxylic Acids Using a Phosphine/Fluoride Deoxyfluorination Reagent System
Munoz, Socrates B.,Dang, Huong,Ispizua-Rodriguez, Xanath,Mathew, Thomas,Prakash, G.K. Surya
supporting information, (2019/03/19)
A fast and simple method for deoxyfluorination of carboxylic acids is presented. The protocol employs commodity chemicals (PPh3, NBS, fluoride), affording products in excellent yields under mild conditions. Acyloxyphosphonium ion, the key reaction intermediate, was identified by NMR spectroscopic methods. Br?nsted acidic conditions are essential for efficient C-F bond formation. The protocol displays scalability, high functional group tolerance, chemoselectivity, and easy purification of products. Deoxyfluorination of active pharmaceutical ingredients was established.
