Divergent Synthesis of Tetrasubstituted Phenols via [3 + 3] Cycloaddition Reaction of Vinyl Sulfoxonnium Ylides with Cyclopropenones

Organic Letters, Год журнала: 2023, Номер 25(23), С. 4286 - 4291

Опубликована: Июнь 2, 2023

Two categories of tetrasubstituted phenols were prepared via the cycloaddition reaction vinyl sulfoxonnium ylides with cyclopropenones in a switchable manner. Copper carbenoid was proposed as active intermediate process 2,3,4,5-tetrasubstituted formation, while 2,3,5,6-tetrasubstituted generated direct [3 + 3] annulation under metal-free conditions. Further synthetic applications also demonstrated.

Язык: Английский

---

Electrochemical Selenylation of Sulfoxonium Ylides for the Synthesis of gem-Diselenides as Antimicrobials against Fungi

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 5572 - 5585

Опубликована: Апрель 21, 2023

Organoselenium compounds are important scaffolds in pharmaceutical molecules. Herein, we report metal-free, electrochemical, highly chemo- and regioselective synthesis of gem-diselenides through the coupling α-keto sulfoxonium ylides with diselenides. The versatility electrochemical manifold enabled selenylation ample scope broad functional group tolerance, as well setting stage for modification complex bioactive Detailed mechanistic studies revealed that key C-Se bond was constructed using n-Bu4NI an electrolyte catalyst electrosynthetic protocol. Finally, desired showed excellent antimicrobial activity against Candida albicans, which can be identified lead further exploration.

Язык: Английский

---

Metal-free cascade O–H double insertion between I^(III)/S^(VI)-ylides, carboxylic acids, and alcohols: modular access to unsymmetrical α,α-O,O-substituted ketones

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(11), С. 3234 - 3241

Опубликована: Янв. 1, 2024

Herein, we present a cascade O–H double insertion reaction between I (III) /S (VI) -ylides, carboxylic acids, and alcohols under metal-free conditions, enabling the modular synthesis of unsymmetrical α,α- O , -substituted ketones.

Язык: Английский

---

A Cascade Rh(III)‐catalyzed C−H Activation/Chemodivergent Annulation of N‐carbamoylindoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone and Tricyclic [1,3]Oxazino[3,4‐a]indol‐1‐ones Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(5), С. 1436 - 1442

Опубликована: Янв. 21, 2021

Abstract A highly efficient cascade Rh(III)‐catalyzed C−H activation/intramolecular chemodivergent cyclization reaction of N‐carbamoylindoles and sulfoxonium ylides has been successfully achieved for the first time. This synergistic process provides rapid access to functionalized dihydropyrimidoindolone tricyclic [1,3]oxazino[3,4‐ a ]indol‐1‐ones skeletons under redox neutral conditions with broad substrate scope remarkable functional‐group compatibility. Further late‐stage modification structurally complex drug molecules mechanistic studies were also accomplished. magnified image

Язык: Английский

---

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

---

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

---

Application of Sulfoxonium Ylides or Iodonium Ylides in Rhodium‐Catalyzed Synthesis of Phenanthrenes

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(8), С. 1744 - 1750

Опубликована: Фев. 22, 2024

Abstract The transmetalation triggered rhodium‐catalyzed C−H bond activation and tandem annulation of 2‐biphenylboronic acids with sulfoxonium ylides or iodonium has been developed. Various products phenanthrenes were constructed under redox‐neutral conditions in 34–86% yields. Several mechanism exploration experiments derivatization reactions conducted sequence to gain a deeper understanding the process potential this transformation. It offers an alternative approach for synthesis phenanthrene derivatives.

Язык: Английский

---

Copper-Mediated Cyclization of Terminal Alkynes with CF₃-Imidoyl Sulfoxonium Ylides To Construct 5-Trifluoromethylpyrroles

Organic Letters, Год журнала: 2024, Номер 26(11), С. 2249 - 2254

Опубликована: Март 7, 2024

A copper-mediated [3 + 2] cyclization of CF3-imidoyl sulfoxonium ylides and terminal alkynes has been demonstrated. This work provides a practical approach for assembling 5-trifluoromethylpyrroles with the merits broad substrate scope, good functional tolerance, mild reaction conditions. Control experiments DFT studies indicate that this may involve addition π-bonds by copper-carbene radicals hydrogen migration.

Язык: Английский

---

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

---

Synthesis of Pyrazolo[1,2‐a]cinnolines via Rhodium(III)‐Catalyzed [4+2] Annulation Reactions of Pyrazolidinones with Sulfoxonium Ylides

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(13), С. 3311 - 3317

Опубликована: Май 8, 2021

Abstract A method to synthesize pyrazolo[1,2‐a]cinnolines via rhodium(III)‐catalyzed C−H activation of pyrazolidinones and subsequent [4+2] annulation sulfoxonium ylides was developed. 5‐Substituted or 5,10‐disubstituted could be obtained by slightly adjusting the reaction conditions. Gram‐scale synthesis practical transformations proved practicability this method. The mechanism proposed in article on basis preliminary mechanistic results previous reports. This features simplified operation, metal‐oxidant free, readily available reactants. magnified image

Язык: Английский

---