Synthesis of α-Carbonyl-α′-amide Sulfoxonium Ylides from Isocyanates with Complete Atom Economy

Organic Letters, Год журнала: 2023, Номер 25(7), С. 1214 - 1217

Опубликована: Фев. 9, 2023

An efficient catalyst- and additive-free facile synthesis of α-carbonyl-α′-amide sulfoxonium ylides from isocyanates β-ketosulfoxonium with complete atom economy has been described. The adorned various functional groups were well-tolerated afforded moderate to high yields the ylide derivatives. Finally, using large-scale reactions converting synthesized into other valuable compounds, we demonstrated practicality this synthetic method.

Язык: Английский

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Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives

Organic Letters, Год журнала: 2020, Номер 22(16), С. 6600 - 6604

Опубликована: Авг. 10, 2020

A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, β-keto thiosulfones, respectively. The nucleophilic addition two molecular to construct sulfone-substituted 1,4-dione compounds the highlight this work.

Язык: Английский

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Annulation of CF₃–Imidoyl Sulfoxonium Ylides with 1,3-Dicarbonyl Compounds: Access to 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles

Organic Letters, Год журнала: 2021, Номер 23(19), С. 7407 - 7411

Опубликована: Сен. 20, 2021

A lithium-bromide-promoted nucleophilic substitution/annulation cascade reaction between CF3-imidoyl sulfoxonium ylides and 1,3-dicarbonyl compounds has been established, the corresponding 1,2,3-trisubstituted 5-trifluoromethylpyrroles have obtained in 27–78% yield. This features a broad substrate scope generates dimethyl sulfoxide H2O as byproducts.

Язык: Английский

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Synthesis of Indenone Derivatives by Rh(III)-Catalyzed C–H Functionalization of Sulfoxonium Ylides with 1,3-Diynes

Organic Letters, Год журнала: 2022, Номер 24(18), С. 3395 - 3400

Опубликована: Май 5, 2022

The transition-metal-catalyzed C-H functionalization of sulfoxonium ylides with alkynes formally participates in [4 + 2] annulations to deliver the naphthol scaffolds. In contrast, herein we disclose first Rh(III)-catalyzed activation, followed by redox-neutral [3 annulation 1,3-diynes, which delivers alkynated indenone derivatives. This protocol features a good functional group tolerance, broad substrate scope, moderate excellent yields, and mild reaction conditions. mechanism was supported through ESI-HRMS characterizing key intermediates catalytic cycle.

Язык: Английский

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Rhodium‐Catalyzed Direct Vinylene Annulation of Sulfoxonium Ylides and N‐carbamoylindoles with Vinylene Carbonate

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(9), С. 1457 - 1464

Опубликована: Апрель 14, 2023

Abstract In this study, Rh(III)‐catalyzed C−H bifunctionalization and direct vinylene annulation of sulfoxonium ylides N ‐carbamoylindoles with carbonate was accomplished, which afforded a series naphthalenones containing β‐ketosulfoxonium ylide moiety, isocoumarins, pyrimidones. This protocol featured mild conditions, broad substrate scope, functional‐groups compatibility. addition, related applications preliminary mechanistic exploratory were also investigated magnified image

Язык: Английский

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Rh(III)‐Catalyzed Diverse C—H Functionalization of Iminopyridinium Ylides

Chinese Journal of Chemistry, Год журнала: 2021, Номер 39(9), С. 2489 - 2494

Опубликована: Май 9, 2021

Main observation and conclusion Divergent synthesis of useful skeletons has been realized via rhodium(III)‐catalyzed C—H activation iminopyridinium ylides coupling with various unsaturated reagents. Isocoumarins isoquinolones were obtained cleavage the C—N or N—N bond in ylidic directing group, while fluorinated alkenes delivered group intact. The reactions occurred wide substrate scopes good efficiency under redox‐neutral air‐tolerant conditions. Representative products exhibit solid‐state fluorescent property bioactivity inhibition toward human cancer cells.

Язык: Английский

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Cobalt(III)-Catalyzed Chemo- and Regioselective [4 + 2]-Annulation of Aromatic Sulfoxonium Ylides with 1,3-Diynes

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(6), С. 4134 - 4153

Опубликована: Март 4, 2022

Air-stable, highly abundant, and cost-effective Co(III)-catalyzed redox-neutral [4 + 2]-annulation of aromatic sulfoxonium ylides with 1,3-diynes providing useful substituted 1-naphthol derivatives in a regioselective manner is described. Further, the prepared 1-naphthols having internal alkyne were converted into polycarbocyclic molecules spiro-dienone good-to-excellent yields. A possible reaction mechanism involving ortho C–H activation as key step was proposed supported by deuterium labeling kinetic isotope studies.

Язык: Английский

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α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C–H activation: a safe carbene precursor and a weak directing group

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 21(5), С. 879 - 909

Опубликована: Дек. 6, 2022

Transition metal-catalyzed cross-coupling of sp2 C-H bonds with diazo compounds via carbene migratory insertion represents an efficient strategy for the construction C-C and C-heteroatom in organic synthesis. Despite popularity as coupling partners activation, they pose serious safety stability issues due to potential exothermic reactions linked release N2 gas. However, compared compounds, sulfoxonium ylides are generally crystalline solids, more stable, widely used industrial scales, easier/safer prepare. Therefore, recent years have witnessed upsurge employing α-carbonyl alternative surrogate transition activation. Unlike contain inherent serve a partner well weak directing group. This review will summarize progress made both categories reactions.

Язык: Английский

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Cascade C–H Activation/Annulation of Sulfoxonium Ylides with Vinyl Cyclopropanes: Access to Cyclopropane-Fused α-Tetralones

Organic Letters, Год журнала: 2023, Номер 25(19), С. 3352 - 3357

Опубликована: Май 4, 2023

Rh-catalyzed weak and traceless directing-group-assisted cascade C–H activation annulation of sulfoxonium ylides with vinyl cyclopropanes as a coupling partner have been accomplished to furnish functionalized cyclopropane-fused tetralones at moderate temperature. The C–C bond formation, cyclopropanation, functional group tolerance, late-stage diversifications drug molecules, scale-up are the important practical features.

Язык: Английский

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Selective Synthesis of Fused Tricyclic [1,3]oxazino[3,4‐a]indolone and Dihydropyrimido [1,6‐a]indolone via Rh(III)‐catalyzed [3+3] or [4+2] C−H Annulation

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 363(2), С. 446 - 452

Опубликована: Дек. 2, 2020

Abstract A formation of fused tricyclic [1,3]oxazino[3,4‐ a ]indol‐1‐ones and dihydropyrimido[1,6‐ ]indol‐1(2 H )‐ones via Rh(III)‐catalyzed [3+3] or [4+2] annulation N ‐methoxy‐1 ‐indole‐1‐carboxamides with sulfoxonium ylides has been developed. These selective reactions were carried out by switching the additives notable features this protocol low catalyst loading broad substrate scope providing corresponding products in up to 99% yields. magnified image

Язык: Английский

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