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Synthesis of acyl fluorides through deoxyfluorination of carboxylic acids

Organic & Biomolecular Chemistry, 2023
A direct deoxyfluorination of carboxylic acids by utilizing KF as fluoride source has been developed. Scale-up reaction could be carried out under the solvent-free conditions, which exhibited the practicability of this reaction in organic synthesis.
Mengjie Cen   +5 more
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Recent Advances in the Synthesis of Acyl Fluorides

Synthesis, 2020
AbstractAcyl fluorides are valuable intermediates in organic synthesis. They are increasingly employed in peptide synthesis, in challenging esterification and amidation reactions or in transition-metal-catalyzed transformations. This review summarizes recent advances in their preparation.1 Introduction2 Nucleophilic Fluorination2.1 α-Fluoroamine ...
Jean-François Paquin   +2 more
openaire   +1 more source

Preparations and reactions of acylated and partially acylated glycosyl fluorides

Carbohydrate Research, 1993
Abstract Partial acylation of glycosyl fluorides in the galacto (2 and 3) and gluco series (8–10) is readily achieved. Attempts to further alkylate these acyl derivatives failed. Treatment of 2 with Lewis acid, however, provided a facile route to the 1,4-anhydro derivative 5 . Lewis acid-mediated glycosylation of 2-acetamido-3,4,6-tri- O -
Joachim Thiem, Matthias Wiesner
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Acyl Fluorides in Late‐Transition‐Metal Catalysis

Angewandte Chemie International Edition, 2019
AbstractIn this Review, we summarize the current state of the art in late‐transition‐metal‐catalyzed reactions of acyl fluorides, covering both their synthesis and further transformations. In organic reactions, the relationship between stability and reactivity of the starting substrates is usually characterized by a trade‐off.
Yohei Ogiwara, Norio Sakai
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Enantioselective acyl-transfer catalysis by fluoride ions

Chemical Communications, 2018
The asymmetric nucleophilic catalysis by fluoride ions at a carbon-based electrophile has been demonstrated for the first time.
Ryan Craig   +3 more
openaire   +2 more sources

Copper‐Catalyzed Asymmetric Acylboration of 1,3‐Butadienylboronate with Acyl Fluorides

Angewandte Chemie International Edition, 2023
AbstractWe report herein a Cu‐catalyzed regio‐, diastereo‐ and enantioselective acylboration of 1,3‐butadienylboronate with acyl fluorides. Under the developed conditions, the reactions provide (Z)‐β,γ‐unsaturated ketones bearing an α‐tertiary stereocenter with high Z‐selectivity and excellent enantioselectivities.
Shang Gao   +3 more
openaire   +2 more sources

Decarboxylative Cross-Coupling of Acyl Fluorides with Potassium Perfluorobenzoates

Organic Letters, 2020
We report the transition metal-free decarboxylative cross-coupling reactions of acyl fluorides with potassium perfluorobenzoates. Compared with traditional transition metal-catalyzed cross-couplings, this protocol presents an extremely environmentally benign pathway to afford unsymmetrical diaryl ketones.
Liyan Fu, Qiang Chen, Yasushi Nishihara
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Quick and easy acyl fluorides

C&EN Global Enterprise, 2017
Tetramethylammonium trifluoromethylthiolate, [N(CH3)4]SCF3, is a mouthful to say, but the inexpensive, bench-stable, and easy-to-use salt has been impressing chemists over the past few years for its versatility in adding SCF3 groups to molecules and as a fluorinating reagent.
openaire   +1 more source

Nickel/copper-cocatalyzed decarbonylative silylation of acyl fluorides

Chemical Communications, 2019
A transformation of acyl fluorides with silylboron via nickel/copper-cocatalysed carbon–fluorine bond cleavage and a sequential decarbonylation, which provides an efficient protocol to functionalize arylsilanes, has been disclosed.
Xiu Wang   +2 more
openaire   +2 more sources

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