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Catalytic Synthesis of Carbonyl Compounds Using Acyl Fluorides, Carbamoyl Fluorides, and Fluoroformates: An Overview

Asian Journal of Organic Chemistry
AbstractAcyl fluorides, carbamoyl fluorides and fluoroformates have been employed as efficient reagents in a number of organic syntheses. Their application in catalytic transformations, however, began to be explored in the early 2000s. Recently, these reagents have increasingly gained attention owing to their unique reactivity in diverse catalytic ...
Yujin Jung, Yoonho Lee, Kwangmin Shin
semanticscholar   +4 more sources

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
openaire   +3 more sources

Versatile Palladium-Catalyzed Approach to Acyl Fluorides and Carbonylations by Combining Visible Light- and Ligand-Driven Operations.

Journal of the American Chemical Society, 2022
We describe the development of a general palladium-catalyzed carbonylative method to synthesize acyl fluorides from aryl, heteroaryl, alkyl, and functionalized organic halides.
Yi Liu   +3 more
semanticscholar   +3 more sources

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   +3 more sources

1,2-Acylcyanation of Styrenes by Photoinduced Nickel Catalysis to Generate Acyl Radicals from Acyl Fluorides

Organic Letters
We report herein a photoinduced nickel-catalyzed 1,2-acylcyanation of styrenes with acyl fluorides and trimethylsilyl cyanide (TMSCN). Nickel(II) acyl complexes, formed from nickel(0) complexes and acyl fluorides, are photoexcited to generate acyl radicals via a ligand-to-metal charge transfer (LMCT) process.
Naoki Oku   +4 more
openaire   +3 more sources

Deoxyfluorination of Carboxylic Acids with CpFluor: Access to Acyl Fluorides and Amides.

Organic Letters, 2021
3,3-Difluoro-1,2-diphenylcyclopropene (CpFluor), a bench-stable fluorination reagent, has been developed in the deoxyfluorination of carboxylic acids to afford various acyl fluorides.
Xiu Wang   +4 more
semanticscholar   +3 more sources

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   +2 more sources

Acid Fluorides as Acyl Electrophiles in Suzuki–Miyaura Coupling

European Journal of Organic Chemistry, 2017
The first palladium‐catalyzed construction of ketones through Suzuki–Miyaura reaction by using acid fluorides is described. In contrast to typical acyl electrophiles such as acid chlorides, acid fluorides are uncommon acyl electrophiles to use in boron‐based coupling reactions, probably due to a high level of stability toward nucleophiles.
Yohei Ogiwara   +3 more
openaire   +3 more sources

Benzoyl Fluorides as Fluorination Reagents: Reconstruction of Acyl Fluorides via Reversible Acyl C–F Bond Cleavage/Formation in Palladium Catalysis

Organometallics, 2020
This report describes the formation of value-added acyl fluorides by means of palladium-catalyzed acyl-exchange reactions between acyl fluorides and acid anhydrides.
Yohei Ogiwara   +2 more
openaire   +2 more sources

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