A Convenient One-Pot Process for Converting Thiols into Sulfonyl Fluorides Using H2O2 as an Oxidant

Synthesis, Год журнала: 2024, Номер unknown

Опубликована: Июль 19, 2024

Abstract A novel protocol for synthesizing sulfonyl fluorides from thiols in one pot is reported. Utilizing SOCl2 and H2O2 as low-cost convenient reagents allows the direct oxidative chlorination of readily available thiol derivatives to give corresponding chlorides, with subsequent fluoride–chloride exchange mediated by KHF2 giving access desired fluorides. This transformation features mild conditions, operational simplicity high efficiency, utilizes a broad substrate scope, including variety aryl, alkyl, benzyl heteroaryl thiols.

Язык: Английский

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Copper-Catalyzed Oxyfluorosulfonylation of β,γ-Unsaturated Oximes with Sulfur Dioxide and Selectfluor for Isoxazoline-Functionalized Aliphatic Sulfonyl Fluorides

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 19, 2024

In this report, we describe a copper-catalyzed cascade reaction involving oxygen radical-induced cyclization/SO

Язык: Английский

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Photoredox-Catalyzed Three-Component Construction of Aryl Sulfonyl Fluoride Using KHF₂: Late-Stage Drug Fluorosulfonylation

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(22), С. 16594 - 16599

Опубликована: Ноя. 1, 2024

Aryl sulfonyl fluorides are prominently featured in organic synthesis and medicinal chemistry. Herein, a metal-free photoredox-catalyzed three-component assembly of aryl fluoride via ammonium salt intermediate has been reported. A variety structurally diverse were synthesized rapidly from dibenzothiophenium (DBT) salts under mild conditions by using KHF2 as the fluorine source. Notably, this methodology can be employed an efficient sustainable approach for late-stage drug fluorosulfonylation. Good yields broad functionality tolerance features methodology. Moreover, derivatization molecules was also demonstrated to showcase its synthetic utility.

Язык: Английский

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1.1 Sulfonyl Fluorides and Acyl Fluorides

Опубликована: Янв. 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.

Язык: Английский

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Progress in Synthesis of Sulfonyl Fluoride

Journal of Organic Chemistry Research, Год журнала: 2023, Номер 11(04), С. 268 - 284

Опубликована: Янв. 1, 2023

Язык: Английский

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