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Mechanochemical Deoxyfluorination of Carboxylic Acids to Acyl Fluorides and Successive Mechanochemical Amide Bond Formation

open access: yesACS Sustainable Chemistry and Engineering
Diverse methods have been reported for the synthesis of acyl fluorides; however, an environmentally benign synthesis method for acyl fluorides remains underdeveloped.
Norio Shibata, Yuji Sumii
exaly   +2 more sources
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Preparation of Acyl Fluorides with Hydrogen Fluoride‐Pyridine and 1,3‐Dicyclohexylcarbodiimide.

ChemInform, 2002
AbstractFor Abstract see ChemInform Abstract in Full Text.
Chinpiao Chen   +2 more
openaire   +1 more source

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
openaire   +1 more source

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
openaire   +2 more sources

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

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
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1.1 Sulfonyl Fluorides and Acyl Fluorides

AbstractSulfonyl fluorides have numerous applications in both synthetic organic chemistry as fluorinating agents and as precursors to sulfur(VI) moieties, and in chemical biology as covalent inhibitors and chemical probes. The utility of sulfonyl fluorides arises from the properties of the S—F bond, as the high bond strength and polarization imparts ...
J. Lai, B. J. Thomson, G. M. Sammis
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