eFluorination for the Rapid Synthesis of Carbamoyl Fluorides from Oxamic Acids

Organic Letters, Год журнала: 2024, Номер 26(29), С. 6103 - 6108

Опубликована: Июль 17, 2024

In this letter, we disclose the anodic oxidation of oxamic acids in presence Et3N·3HF as a practical, scalable, and robust method to rapidly access carbamoyl fluorides from readily available stable precursors. The simplicity also led us develop first flow electrochemical preparation fluorides, demonstrating scale-up feasibility proof concept.

Язык: Английский

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

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(5)

Опубликована: Фев. 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.

Язык: Английский

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Facile Synthesis of Carbamoyl Fluorides via N-Carbamoylimidazole Activation

ACS Omega, Год журнала: 2025, Номер 10(7), С. 6908 - 6917

Опубликована: Фев. 14, 2025

The untapped potential of carbamoyl fluorides for various chemico/biological applications is hampered by the scarcity straightforward and benign methods their synthesis. In this report, we disclose a novel mild three-step procedure that avoids exotic, corrosive, highly toxic reagents. Briefly, commercially available secondary amines are carbamoylated with 1,1′-carbonyldiimidazole, followed alkylation to improve nucleofugality, exchange inorganic KF. This works on gram scale without chromatographic purification. It however limited basic, sterically unhindered alkylation-prone functional groups.

Язык: Английский

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Synthesis of Alkyl Sulfones via a Photocatalytic Multicomponent Reaction of Aryldiazo Tetrafluoroborate Salts, Styrene Derivatives, and Sodium Metabisulfite

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 25, 2024

Practical visible-light-induced synthesis of alkyl sulfones has been achieved via a multicomponent reaction aryldiazo tetrafluoroborate salts, styrene derivatives, thiophenol and sodium metabisulfite in the presence rhodamine B.

Язык: Английский

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Visible-light-promoted one-pot synthesis of β-keto sulfones from aryldiazo tetrafluoroborate salts via aerobic multicomponent reaction

Tetrahedron, Год журнала: 2024, Номер 167, С. 134303 - 134303

Опубликована: Окт. 10, 2024

Язык: Английский

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DDQ-catalyzed oxidative α-allylation of isochromans under aerobic conditions

RSC Advances, Год журнала: 2024, Номер 14(53), С. 39645 - 39652

Опубликована: Янв. 1, 2024

A direct C–H activation of isochromans using a DDQ/TBN/O 2 catalytic system, followed by addition allylstannane in the presence methanesulfonic acid, provides various α-allyl substituted efficiently.

Язык: Английский

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