Decarboxylative Sulfonylation of Carboxylic Acids under Mild Photomediated Iron Catalysis

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2381 - 2386

Published: March 15, 2024

Organic sulfones are an important class of chemical compounds widely used in many research fields. The direct decarboxylative sulfonylation carboxylic acids is attractive but challenging, particularly when iron as a metal catalyst. Herein, we describe photoinduced iron-catalytic method for the synthesis directly using via radical-based decarboxylation. This protocol mild, highly efficient, and easy-to-operate. A broad scope carbon electrophiles could be well tolerated. mechanism involving iron-catalyzed decarboxylation, radical transfer, single-electron reduction, nucleophilic attack proposed.

Language: Английский

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Recent Advances in Developing Radical Methods for the Synthesis of Aliphatic Sulfonyl Fluorides

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(23)

Published: May 25, 2024

Abstract Sulfonyl fluorides have widespread applications in many fields, including organic synthesis, chemical biology, drug discovery and materials science. In particular, the past decade, a number of aliphatic sulfonyl been identified showing various biological activities. These appealing features brought about significant advancement developing synthetic methods to access fluorides. this review, we will discuss recent developments radical approaches for synthesis

Language: Английский

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Copper-Catalyzed Chemoselective (Amino)fluorosulfonylation of Hydrocarbons via Intramolecular Fluorine-Atom Transfer

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(6), P. 4318 - 4328

Published: March 6, 2024

Sulfonyl fluorides have found increasing applications as functional molecules in chemistry and biology. We herein report a copper-catalyzed atom-economical access to two categories of sulfonyl through radical relay strategy the presence an SO2 surrogate. The aliphatic C(sp3)–H bond N-fluoro-N-alkyl sulfonamides reacted via 1,5-hydrogen atom transfer (HAT) process, affording alkanesulfonyl with proximal amino group. On other hand, utilizing substrates containing proper C═C double resulted intramolecular olefin aminofluorosulfonylation, allowing synthesis fluorosulfonyl-functionalized pyrrolidines piperidines atom-transfer addition (ATRA). Both reaction systems proceeded under mild conditions, requiring no additional fluorine source. Experimental computational studies suggest that S–F coupling is likely achieved radical-rebound pathway. By taking advantage SuFEx multifunctionality products, method applicable late-stage modification bioactive compounds, drug ligation chemistry, organic synthesis.

Language: Английский

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Recent advances in photochemical and electrochemical strategies for the synthesis of sulfonyl fluorides

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(1), P. 217 - 235

Published: Nov. 14, 2023

This review summarizes the latest achievements in photochemical and electrochemical strategies for synthesis of sulfonyl fluorides focuses on novel features proposed mechanisms.

Language: Английский

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Radical Hydro-Fluorosulfonylation of Propargylic Alcohols via Electron Donor–Acceptor Photoactivation

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1410 - 1415

Published: Feb. 15, 2024

A radical hydro-fluorosulfonylation of propargyl alcohols with FSO2Cl is presented based on the photoactivation electron donor–acceptor (EDA) complex. The reaction avoids requirement for photocatalysts, bases, hydrogen donor reagents, any other additives, and harsh conditions, enabling facile synthesis various functionalized γ-hydroxy (E)-alkenylsulfonyl fluorides. These multifunctional sulfonyl fluorides can be further diversified, providing access to privileged molecules biological relevance.

Language: Английский

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Switchable carbo-fluorosulfonylation and hydro-fluorosulfonylation of alkenes enabled by bifunctional fluorosulfonyl radical precursors

Chem Catalysis, Journal Year: 2023, Volume and Issue: 3(12), P. 100821 - 100821

Published: Nov. 28, 2023

Language: Английский

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Iodine(III)-Containing Reagents in Photo-Assisted and Photo-Catalyzed Organic Synthesis

Molecules, Journal Year: 2025, Volume and Issue: 30(4), P. 784 - 784

Published: Feb. 8, 2025

Iodine(III) reagents have become a highly relevant tool in organic synthesis due to their great versatility as strong but green oxidants. Several transformations involving cyclizations well functionalization of different cores been broadly described and reviewed. Herein, the participation these photochemical exclusively by direct irradition or photoredox cycles using some transition metals, will be briefly plausible further that potentially can developed.

Language: Английский

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A Completely Metal‐Free Protocol for Oxidative Desulfitative C‐N Coupling Reaction in Non‐Basic Condition

Chemistry - An Asian Journal, Journal Year: 2025, Volume and Issue: unknown

Published: March 11, 2025

Abstract A metal free oxidative desulfitative C−N coupling reaction through activation of latent thiol group using hypervalent iodine reagent is being reported in eco‐friendly solvent ethanol. Here, the thio‐amide present 5‐alkylidene‐rhodanine has been utilized as functionality and with amines realized. The occurs evading use catalysts, inert atmosphere, high temperature or microwave heating, strong base which normally required for catalyzed reaction. Pertinently, here poorly nucleophilic aromatic react very efficiently. Desulfitative involving moiety condition never accomplished one step, without requiring heating bases. at just 50 °C few hours under ambient atmosphere. Moreover, no H 2 S released environment, since solid sulphur precipitated out side product, making this protocol environmentally friendly. Metal condition, low temperature, non‐toxic reagent, prevention release environment make much friendly highly suitable a sustainable way.

Language: Английский

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Recent progress in sulfonyl fluoride synthesis via the radical sulfur dioxide insertion and fluorination strategy

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 8, 2024

Language: Английский

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Copper-Catalyzed, Interrupted Remote Fluoromethylthiolation of Unactivated C(sp3)-H Bonds

Organic Letters, Journal Year: 2024, Volume and Issue: 26(10), P. 2068 - 2072

Published: March 1, 2024

An efficient copper-catalyzed selective fluoromethylthiolation of an inert δ-C(sp3)–H bond in sulfonamides was reported. In the presence a copper catalyst and PhSO2SRf, radical generated through 1,5-hydrogen atom transfer (HAT) sufficiently trapped by instead copper, which prevalent metal-catalyzed radical-relay processes, incorporating fluoromethylthio group into molecules. The general substrate scope mild conditions endowed method with wide potential applications pharmaceuticals agrochemicals.

Language: Английский

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