1.1 Sulfonyl Fluorides and Acyl Fluorides DOI
Joey Lai, Brodie J. Thomson, Glenn M. Sammis

et al.

Published: Jan. 1, 2024

Abstract Sulfonyl fluorides have numerous applications in both synthetic organic chemistry as fluorinating agents and precursors to sulfur(VI) moieties, chemical biology covalent inhibitors probes. The utility of sulfonyl arises from the properties S—F bond, high bond strength polarization imparts stability chemoselectivity that differentiates this group other halides. Likewise, acyl found widespread use synthesis reactive intermediates. increased toward hydrolysis aminolysis comparison chlorides bromides are a result relative electrostatic C—F bond. In review, we provide an overview approaches these valuable motifs, with focus on versatile easy-to-handle protocols.

Language: Английский

Electrochemical Fluorination of Organic Compounds Using a Hexafluorosilicate Salt as an Inexpensive and Widely Available Fluorine Source DOI

David M. Köpfler,

Gabriele Laudadio,

Clara Bovino

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(4), P. 1084 - 1088

Published: Jan. 20, 2025

The introduction of fluorine into organic molecules is the utmost importance in preparation active pharmaceutical ingredients (APIs). While a wide range sources for synthesis have been used over past decades, associated safety risks, cost, or environmental impact are still serious limitations. Hexafluorosilicate salts one most inexpensive and readily available nucleophilic fluorine, but they so far not synthesis. Herein we report first example use hexafluorosilicate salt as reagent formation C-F bonds. We selected model reaction an electrochemical decarboxylative fluorination procedure. bis(5-ethyl-2-methylpyridin-1-ium) hexafluorosilicate(IV) was key to obtaining soluble reactive salt. This protocol enabled primary, secondary, tertiary aliphatic fluorides (22 examples) up 85% yield. method also successfully transferred flow electrolysis cell, demonstrating its robustness scalability. Finally, extended scope source by applicability benzylic C-H fluorination.

Language: Английский

Citations

1
Recent advances exploiting reactive intermediates generated via continuous flow chemistry DOI Creative Commons
Arlene Bonner, Parth Naik, Ruairi Crawford

et al.

Current Opinion in Green and Sustainable Chemistry, Journal Year: 2024, Volume and Issue: 47, P. 100907 - 100907

Published: March 13, 2024

Reactive intermediates are transient high-energy species playing a pivotal role in the synthesis of organic molecules. Continuous flow processing is frequently exploited generating plethora reactive situ followed by their rapid transformation to target Reactor miniaturisation along with high heat and mass transfer rates key features that these processes provide for additional benefits such as safety scalability. This short review highlights recent advances field chemistry generation use photochemical reactions, low-temperature sequences well related transformations.

Language: Английский

Citations

3
Deoxyfluorination of Ketones with Sulfur Tetrafluoride (SF4) and Dialkylamines in Continuous Flow Mode DOI
Dominik Polterauer, Simon Wagschal,

Michael Bersier

et al.

Organic Process Research & Development, Journal Year: 2024, Volume and Issue: 28(7), P. 2919 - 2927

Published: July 8, 2024

Language: Английский

Citations

3
On‐Demand Continuous Flow Synthesis of Pentafluorosulfanyl Chloride (SF5Cl) Using a Custom‐Made Stirring Packed‐Bed Reactor DOI Creative Commons
Lauriane C. Peyrical, Thibaud Mabit, Vanessa Kairouz

et al.

Chemistry - A European Journal, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 15, 2025

The pentafluorosulfanyl (SF5-) group has been the subject of a surge interest in past decade, but there is still little practicality associated with its synthesis and installation. Herein reported first continuous flow chloride (SF5Cl), most common reagent for SF5-substituted compounds. based on inexpensive easy-to-handle reagents: sulfur powder (S8), trichloroisocyanuric acid (TCCA) potassium fluoride (KF). To this end, custom-made stirring reactor was designed to allow fast, safe, highly efficient on-demand SF5Cl. resulting SF5Cl solution showcased radical addition alkynes telescoped fashion.

Language: Английский

Citations

0
Recent advances in fluorine chemistry using flow technology DOI
Kensuke Muta, Hiroki Soutome, Aiichiro Nagaki

et al.

Journal of Fluorine Chemistry, Journal Year: 2024, Volume and Issue: 279, P. 110349 - 110349

Published: Sept. 14, 2024

Language: Английский

Citations

1
Preparation of Sulfonyl Chlorides by Oxidative Chlorination of Thiols and Disulfides using HNO3/HCl/O2 in a Flow Reactor DOI

Niklas Sulzer,

Dominik Polterauer, Christopher A. Hone

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: 17(15)

Published: March 13, 2024

Abstract A continuous flow metal‐free protocol for the synthesis of sulfonyl chlorides from thiols and disulfides in presence nitric acid, hydrochloric acid oxygen was developed. The influence reaction parameters investigated under batch conditions. Online 19 F NMR successfully implemented to investigate different conditions within a single experiment. were isolated (mostly 70–81 % yield) after performing simple aqueous washing procedure. In particular, operated >6 hours convert diphenyl disulfide its corresponding chloride, achieving throughput 3.7 g h −1 . environmental impact assessed compared an existing using 1,3‐dichloro‐5,5‐dimethylhydantoin (DCH) as reagent. process mass intensity (PMI) newly‐developed (15) favorably DCH (20).

Language: Английский

Citations

0
1.1 Sulfonyl Fluorides and Acyl Fluorides DOI
Joey Lai, Brodie J. Thomson, Glenn M. Sammis

et al.

Published: Jan. 1, 2024

Abstract Sulfonyl fluorides have numerous applications in both synthetic organic chemistry as fluorinating agents and precursors to sulfur(VI) moieties, chemical biology covalent inhibitors probes. The utility of sulfonyl arises from the properties S—F bond, high bond strength polarization imparts stability chemoselectivity that differentiates this group other halides. Likewise, acyl found widespread use synthesis reactive intermediates. increased toward hydrolysis aminolysis comparison chlorides bromides are a result relative electrostatic C—F bond. In review, we provide an overview approaches these valuable motifs, with focus on versatile easy-to-handle protocols.

Language: Английский

Citations

0