The synthesis of acyl fluorides using the deoxofluorination reaction of carboxylic acids using XtalFluor-E is described. This transformation, assisted by a catalytic amount of NaF, occurs at room temperature in EtOAc, where XtalFluor-E behaves as the activating agent and the fluoride source. A wide range of acyl fluorides were obtained in moderate to excellent yields (36-99%) after a simple filtration on a pad of silica gel. We also demonstrated that sequential deoxofluorination/amidation was possible.
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http://dx.doi.org/10.1021/acs.joc.0c01377 | DOI Listing |
Acta Crystallogr C Struct Chem
February 2025
Department Chemie, Ludwig-Maximilians Universität, Butenandtstrasse 5-13 (Haus D), D-81377 München, Germany.
Acyl fluorides and acyl cations represent typical reactive intermediates in organic reactions, such as Friedel-Crafts acylation. However, the comparatively stable phenyl-substituted compounds have not been fully characterized yet, offering a promising backbone. Attempts to isolate the benzoacylium cation have only been carried out starting from the acyl chloride with weaker chloride-based Lewis acids.
View Article and Find Full Text PDFArch Biochem Biophys
January 2025
Department of Biosciences Grand Asian University of Sialkot, Pakistan.
Acyl thiourea scaffolds are frequently employed in drug development to discern unique and essential therapies for the eradication of the most challenging diseases. Hence, we developed a library of novel cyclopropyl incorporating acyl thiourea derivatives (4a-j) and evaluated their antimicrobial, α-amylase, and proteinase K inhibition potential. Compound (4h) (4-methoxy) demonstrated the strongest α-amylase inhibition (IC = 1.
View Article and Find Full Text PDFChemistry
December 2024
Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064, P. R. China.
Trifluoromethylarenes (ArCF) are crucial bioisosteres in medicinal chemistry, but catalyst-free and controlled photo-activation of the ArC(sp)-F bond remains a significant challenge. The photo-induced defluorination acyl fluoride exchange (photo-DAFEx) of m-trifluoromethylaniline, induced by ultraviolet light, emerges as a promising novel photo-click reaction for photoaffinity drug discovery. However, the photophysical properties of NMePhFC(sp)-F derivatives and factors affecting ArC(sp)-F bond activation in photo-DAFEx are not yet fully understood, hindering the development of new photo-defluorination reagents with longer absorption wavelength for the photo-DAFEx.
View Article and Find Full Text PDFAcc Chem Res
November 2024
State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou 730000, China.
Org Biomol Chem
December 2024
Continuous Flow Engineering Laboratory of National Petroleum and Chemical Industry, Changzhou University, Changzhou, Jiangsu 213164, China.
We report an efficient photocatalytic protocol for the defluorocyanoalkylation and defluoroacylation of α-trifluoromethyl styrenes by utilizing oxime esters as radical donors, allowing for the preparation of diverse -difluoroalkenes. The treatment of α-trifluoromethyl styrenes with cyclobutanone oxime esters led to the formation of distal cyano group-anchored -difluoroalkenes. Notably, adding KCO as an inorganic base to the photocatalytic system afforded γ,γ-difluoroallylic ketones by utilizing acyl oxime esters as the acylating agents.
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