87102-73-6Relevant academic research and scientific papers
METHOD AND REAGENT FOR DEOXYFLUORINATION
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Paragraph 0111-0112; 0114-0115; 0117, (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.
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).
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
, (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.
Low-Resolution Microwave Studies of Substituted Ethyl- and Isopropylbenzenes
True, Nancy S.,Farag, Maya, S.,Bohn, Robert K.,MacGregor, Malcolm A.,Radhakrishnan, J.
, p. 4622 - 4627 (2007/10/02)
A single conformation exists in ethylbenzenes with the ethyl C-C bond lying in a plane orthogonal to the benzene ring.This conclusion results from the observation that asymmetrically substituted ethylbenzenes each display only a single band series in low-resolution microwave (LRMW) spectra whereas any other conformation of the ethylphenyl fragment would result in two spectroscopically distinguishable species.LRMW spectra of isopropylbenzene derivatives display three spectroscopically distinguishable band series, two of which correspond to the conformation with the methine C-H bond eclipsed with the benzene ring and syn or anti with respect to an unsymmetrical phenyl substituent.The third series is much more intense, has a B + C value which is the average of the syn and anti forms, and is consistent with the superposition of spectra of torsionally excited species.
