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

Science China Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 8, 2024

Язык: Английский

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Regioselective 1,4-Addition of P(O)–H Species to In Situ-Formed 1-Benzopyrylium Ion from C3-Substituted 2H-Chromene Hemiketals to Construct C3-Functionalized C4-Phosphorylated 4H-Chromenes

The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(5), С. 1768 - 1783

Опубликована: Янв. 24, 2025

Herein, we report the first example that P(O)-H species including H-phosphonates and H-phosphine oxides could participate in a highly regioselective 1,4-addition to situ generated 1-benzopyrylium ion from C3-substituted 2H-chromene hemiketals, which provides brand-new effective approach for synthesis of C4-phosphorylated 4H-chromenes with diverse C3-functionality (ketone, ester, sulfonyl, aryl, alkyl groups). In total, reaction features use inexpensive Zn(ClO4)2·6H2O as catalyst, low catalyst loading (only 5 mol %), mild conditions (60 °C, 10 min 24 h), broad substrate scope (46 examples) well good high yields (>90% yield on average). More importantly, mechanistic experiments demonstrated essential role C3-substituent hemiketals stabilizing control.

Язык: Английский

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Pd-Catalyzed Asymmetric Synthesis of Chiral 2-Trifluoromethyl-4-(indol-3-yl)-4H-chromene Derivatives

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 29, 2025

This paper presents a new strategy for the construction of chiral 4H-chromene skeleton. A series 2-trifluoromethyl-4-(indol-3-yl)-4H-chromenes were synthesized in moderate to good yields (60-92%) with excellent enantioselectivity (up 97% ee) through palladium-catalyzed asymmetric condensation 2H-chromenes and indoles. These trifluoromethylated, stereochemically rich building blocks hold potential value medicinal chemistry.

Язык: Английский

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Electrochemical Radical Fluorosufonylation of Allyl Bromides

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 20, 2025

A radical fluorosulfonylation of allyl bromides was achieved under electroreductive conditions. This catalyst-free protocol employs mild conditions and enables straightforward access to a new structurally diverse variety previously inaccessible sulfonyl fluorides. We have also illustrated the synthetic value this method by performing scaled-up reactions product derivatization.

Язык: Английский

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Stereoselective addition of phenols to 2-chloroprop-2-ene-1-sulfonyl fluoride (CESF) for the synthesis of a class of novel vinyl sulfonyl fluorides

New Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

We report a novel, rapid, metal-free method for vinyl ether synthesis, integrating sulfonyl fluoride group under mild conditions in 10 min. This efficient strategy enables diverse compounds, revolutionizing industrial synthesis.

Язык: Английский

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A simple protocol for stereoselective construction of novel β-sulfanyl vinyl sulfonyl fluorides

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

The addition of thiols to 2-bromoprop-2-ene-1-sulfonyl fluoride (BPESF) in the presence an organic base has been successfully employed for synthesis highly functionalized sulfanyl vinyl sulfonyl fluorides with 100% stereoselectivity.

Язык: Английский

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TfOH-catalysed PPh3-Promoted Nucleophilic Cyclization Reactions for the Synthesis of Functionalized (Z)-2-imino-benzo[e][1,3]thiazin-4-ones

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134676 - 134676

Опубликована: Апрель 1, 2025

Язык: Английский

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Research Progress on the Synthesis of Sulfonyl Fluoride Compounds Based on Small Molecule Sulfur-Fluoride Building Blocks

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(4), С. 1223 - 1223

Опубликована: Янв. 1, 2025

Язык: Английский

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The construction of novel pyrrole-4H-chromene-embedded vinyl sulfonyl fluorides via a three-component process

New Journal of Chemistry, Год журнала: 2024, Номер 48(33), С. 14532 - 14537

Опубликована: Янв. 1, 2024

A synthetic strategy involving salicylaldehyde, 2-chloroprop-2-ene-1-sulfonyl fluoride (CESF), and pyrrole has been developed to construct novel pyrrole-4 H -chromene-embedded vinyl sulfonyl derivatives with exclusive regioselectivity.

Язык: Английский

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Synthesis of α-Bromo Arylethyl Sulfonyl Fluorides and β-Arylethenesulfonyl Fluorides via Copper-Catalyzed Meerwein Arylation

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(18), С. 13709 - 13718

Опубликована: Авг. 16, 2024

A practical copper-catalyzed process for the synthesis of β-arylethenesulfonyl fluorides is described. series α-bromo arylethyl sulfonyl was prepared via Meerwein reaction from arenediazonium tetrafluoroborates and ethenesulfonyl fluoride (ESF) under mild conditions. The following were further obtained through a β-elimination reaction. This protocol features excellent regio- stereoselectivity broad substrate scope.

Язык: Английский

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