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

ACS Catalysis, Год журнала: 2024, Номер 14(6), С. 4318 - 4328

Опубликована: Март 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.

Язык: Английский

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Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(5)

Опубликована: Апрель 8, 2023

Abstract Ring‐fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction such from readily available substrates becomes an important researching topic organic synthesis. Triggered by addition radicals to (activated or unactivated) double bonds alkenes, subsequent intramolecular addition/cyclization leads compounds. Following this procedure, variety functionalized ring‐fused were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, operational simple approaches toward versatile alkene‐based substrates. Here, we summarized recent on formation via radical‐triggered cascade reactions alkenes. Construction with no less than 3 fused rings developed during last decade included Review, corresponding mechanisms also discussed.

Язык: Английский

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Enantioselective synthesis of chiral sulfones by hydrogen-bonding/organophotoredox co-catalyzed asymmetric sulfonylation

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(9), С. 2251 - 2256

Опубликована: Янв. 1, 2023

We report an enantioselective sulfonylation of α,β-unsaturated carbonyl compounds with 4-alkyl substituted Hantzsch esters and DABCO·(SO 2 ) by interfacing photoredox hydrogen bonding catalysis.

Язык: Английский

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Metal-free photosensitized aminosulfonylation of alkenes: a practical approach to β-amido sulfones

Green Chemistry, Год журнала: 2023, Номер 25(10), С. 3857 - 3863

Опубликована: Янв. 1, 2023

A general and environmentally friendly organic photo-induced strategy was developed for the synthesis of diverse alkyl-substituted β-amino sulfone derivatives, including primary, secondary, tertiary products.

Язык: Английский

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Visible-light-induced alkoxycarbonylation/cyclization of 1,7-enynes: synthesis of dihydropyranones containing all-carbon quaternary centers

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(8), С. 2018 - 2023

Опубликована: Янв. 1, 2023

A photoredox catalyzed radical-triggered tandem cyclization of 1,7-enynes with alkyloxalyl chlorides is developed, leading to dihydropyranones containing all-carbon quaternary centers through alkoxycarbonylation/dicyclization 1,7-enynes.

Язык: Английский

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The Application of Sulfonyl Hydrazides in Electrosynthesis: A Review of Recent Studies

ACS Omega, Год журнала: 2022, Номер 7(44), С. 39531 - 39561

Опубликована: Окт. 27, 2022

Sulfonyl hydrazides are viewed as alternatives to sulfinic acids and their salts or sulfonyl halides, which broadly used in organic synthesis work active pharmaceutical substances. Generally, considered good building blocks show powerful value a diverse range of reactions construct C–S bonds C–C bonds, even C–N sulfur, carbon, nitrogen sources, respectively. As profound synthetic tool, the electrosynthesis method was recently achieve efficient green applications hydrazides. Interestingly, many unique novel electrochemical syntheses using radical precursors have been developed, including cascade reactions, functionalization heterocycles, well continuous flow combining with since 2017. Accordingly, it is necessary specifically summarize recent developments only more deeply understand better design reactions. Herein, research 2017 reviewed detail based on chemical structures products reaction mechanisms.

Язык: Английский

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Anti-α-Glucosidase, SAR Analysis, and Mechanism Investigation of Indolo[1,2-b]isoquinoline Derivatives

Molecules, Год журнала: 2023, Номер 28(13), С. 5282 - 5282

Опубликована: Июль 7, 2023

To find potential α-glucosidase inhibitors, indolo[1,2-b]isoquinoline derivatives (1–20) were screened for their inhibitory effects. All presented effects with IC50 values of 3.44 ± 0.36~41.24 0.26 μM compared to the positive control acarbose (IC50 value: 640.57 5.13 μM). In particular, compound 11 displayed strongest anti-α-glucosidase activity, being ~186 times stronger than acarbose. Kinetic studies found that compounds 9, 11, 13, 18, and 19 all reversible mix-type inhibitors. The 3D fluorescence spectra CD results revealed interaction between changed conformational changes α-glucosidase. Molecular docking molecular dynamics simulation indicated addition, cell cytotoxicity drug-like properties also investigated.

Язык: Английский

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Recent Advances in Nickel-Catalyzed Ring Opening Cross-Coupling of Aziridines

Acta Chimica Sinica, Год журнала: 2024, Номер 82(2), С. 190 - 190

Опубликована: Янв. 1, 2024

Язык: Английский

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Visible-Light-Induced Synthesis of Alkylsulfonated Isoquinolinones from 2-Aryl Indoles/Benzimidazoles through Insertion of Sulfur Dioxide

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(13), С. 9293 - 9305

Опубликована: Июнь 7, 2023

A visible-light-induced three-component reaction of 2-aryl indoles/benzimidazoles, Hantzsch esters, and sodium pyrosulfite through a radical cascade cyclization process with the insertion sulfur dioxide is described. It provides novel powerful way for synthesis alkylsulfonated isoquinolinones. esters Na2S2O5 are employed as alkyl precursors SO2 surrogate, respectively. This transformation exhibits good functional group tolerance substrate applicability under mild conditions.

Язык: Английский

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Catalyst-Free Radical Dearomatization of Phenols with Aryldiazonium Tetrafluoroborates and DABCO·(SO2)2

Synlett, Год журнала: 2025, Номер unknown

Опубликована: Март 4, 2025

Abstract A catalyst-free, three-component dearomatization of phenols with aryldiazonium tetrafluoroborates and DABCO·(SO2)2 has been developed for the synthesis 4-(arylsulfonyl)cyclohex-2,5-dien-1-one scaffolds. This method offers mild reaction conditions high step efficiency, providing a green efficient strategy phenols. Mechanistic studies indicated that this transformation relies on tandem radical sulfur dioxide insertion process.

Язык: Английский

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