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

ACS Sustainable Chemistry & Engineering, Journal Year: 2024, Volume and Issue: 12(9), P. 3565 - 3574

Published: Feb. 16, 2024

Diverse methods have been reported for the synthesis of acyl fluorides; however, an environmentally benign method fluorides remains underdeveloped. In this study, we developed solvent-free mechanochemical deoxyfluorination carboxylic acids to mediated by 1,1,2,2-tetrafluoroethyl-N,N-dimethylamine (TFEDMA) using a ball mill. This facilitated high product yields in short reaction times even sterically challenged acids. We also realized coupling and amines as well TFEDMA-mediated direct with via sequential one-pot deoxyfluorination/coupling pathway. Furthermore, protocol was expanded include peptide synthesis. The efficiency protocol, terms speed, characteristics, favorable E-factor, aligns requirements current environmental policies.

Language: Английский

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Unlocking the Power of Acyl Fluorides: A Comprehensive Guide to Synthesis and Properties

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(18)

Published: March 6, 2024

Abstract Acyl fluorides have emerged as versatile reagents in various synthetic endeavors, offering a range of advantages over their counterparts, acyl chlorides. This study delves into the properties and reactivity fluorides, particularly reaction with amines alcohols, to elucidate distinct characteristics. We also introduce facile practical synthesis from stable solution CF 3 O − salt. Additionally, we establish an efficient one‐pot process for direct preparation amides or esters corresponding acids showcasing remarkable efficiency these transformations.

Language: Английский

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Nitrogen-Based Organofluorine Functional Molecules: Synthesis and Applications

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Fluorine and nitrogen form a successful partnership in organic synthesis, medicinal chemistry, material sciences. Although fluorine-nitrogen chemistry has long rich history, this field received increasing interest made remarkable progress over the past two decades, driven by recent advancements transition metal organocatalysis photochemistry. This review, emphasizing contributions from 2015 to 2023, aims update state of art synthesis applications nitrogen-based organofluorine functional molecules chemistry. In dedicated sections, we first focus on fluorine-containing reagents organized according type groups attached nitrogen, including N-F, N-RF, N-SRF, N-ORF. review also covers nitrogen-linked building blocks, catalysts, pharmaceuticals, agrochemicals, underlining these components' broad applicability growing importance modern

Language: Английский

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Elemental Sulfur-Mediated Aromatic Halogenation

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 770 - 777

Published: Dec. 19, 2023

A method for aromatic halogenation using a combination of elemental sulfur (S8) and N-halosuccinimide has been developed. catalytic quantity with N-bromosuccinimide (NBS) N-chlorosuccinimide (NCS) effectively halogenated less-reactive compounds, such as ester-, cyano-, nitro-substituted anisole derivatives. No reaction occurred in the absence S8, underscoring its crucial role activity. This system was also applicable to iodination 1,3-diiodo-5,5-dimethylhydantoin.

Language: Английский

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

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(5)

Published: Feb. 1, 2024

Abstract Acyl fluorides, carbamoyl fluorides and fluoroformates have been employed as efficient reagents in a number of organic syntheses. Their application catalytic transformations, however, began to be explored the early 2000s. Recently, these increasingly gained attention owing their unique reactivity diverse systems. This review aims overview advancements development processes, including transition‐metal catalysis, organocatalysis, cooperative NHC/photoredox where organofluorine compounds are acyl, carbamoyl, ester group donors.

Language: Английский

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Synthesis of Acyl Halides from Carboxylic Acid Thioesters for Synthesis of Ketones, Esters, Amides and Peptides

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 4061 - 4065

Published: July 19, 2024

Abstract A synthesis of acyl halides from the corresponding carboxylic acid thioesters was achieved using commercially available Selectfluor or NCS, and fluoride chloride intermediates were transformed to esters, amides, several carbon‐carbon bond formation products. This approach can be applied peptide functionalized amino thioesters.

Language: Английский

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1.1 Sulfonyl Fluorides and Acyl Fluorides

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

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