Recent Developments in Stereoselective Reactions of Sulfoxonium Ylides DOI Creative Commons

Ciarán O’Shaughnessy,

Mukulesh Mondal,

Nessan J. Kerrigan

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(3), P. 655 - 655

Published: Feb. 1, 2025

This review probes the recent developments in stereoselective reactions within area of sulfoxonium ylide chemistry since early 2000s. An abundance research has been applied to its emergence 1960s. There a continued effort then with work traditional areas, such as epoxidation, aziridination and cyclopropanation. Efforts have also novel olefination insertion reactions, develop methodologies using organocatalysis transition metal catalysis. The growing interrupted Johnson–Corey–Chaykovsky is described, whereby unexpected cyclopropanation epoxidation developed. In general, most observed mechanistic pathway ylides formal cycloaddition: (2 + 1) (e.g., epoxides, cyclopropanes, aziridines), (3 oxetanes, azetidines), (4 indanones, indolines). involves formation zwitterionic intermediate through nucleophilic addition carbanion an electrophilic site. intramolecular cyclization occurs, constructing cyclic product. Insertion X–H bonds X = S, N or P) are observed, protonation followed by X, form inserted

Language: Английский

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

Ajay Kant Gola,

Ajay Sharma, Satyendra Kumar Pandey

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(7), P. 1214 - 1217

Published: Feb. 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.

Language: Английский

Citations

18
A Platform for the Synthesis of Diverse Phosphonyl and Thiofunctionalized Sulfoxonium Ylides DOI

Wen‐Xuan Zou,

Qiong Hu,

Dan‐Ting Shen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5811 - 5816

Published: June 28, 2024

A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization hybrid I(III)/S(VI) is presented. This process allows efficient P–H insertion under Cu catalysis, enabling synthesis ylides, whereas reaction with sulfur-containing reagents including AgSCF3, KSC(S)OR, KSCN mild conditions resulted in α-trifluoromethylthiolation, dithiocarbanation, thiocyanation accordingly. Of note, wide substrate compatibility (108 examples), excellent efficiency (up to 99% yield), gram-scale experiments, various product derivatizations highlight synthetic utility this protocol.

Language: Английский

Citations

7
Palladium-Catalyzed Synthesis of Bis-Substituted Sulfoxonium Ylides DOI

Christopher Janot,

Pierre Palamini,

Benjamin C. Dobson

et al.

Organic Letters, Journal Year: 2018, Volume and Issue: 21(1), P. 296 - 299

Published: Dec. 20, 2018

The lack of general access to bis-substituted sulfoxonium ylides is addressed by developing a palladium-catalyzed C–H cross-coupling α-ester with (hetero)aryl iodides, bromides, and triflates. Three different catalysts have been evaluated. This method amenable the late-stage functionalization active pharmaceutical ingredients.

Language: Английский

Citations

50
Iridium-Catalyzed Three-component Coupling Reaction of Carbon Dioxide, Amines, and Sulfoxonium Ylides DOI
Huanfeng Jiang, Hao Zhang, Wenfang Xiong

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(4), P. 1125 - 1129

Published: Feb. 4, 2019

The first iridium-catalyzed three-component coupling reaction of carbon dioxide, amines, and sulfoxonium ylides has been developed, providing an efficient straightforward method for the construction a range structurally diverse O-β-oxoalkyl carbamates in moderate to excellent yields. This novel protocol features use readily available substrates, wide substrate scope, good functional group tolerance. Moreover, phosgene-free strategy was successfully applied synthesis potential antitumor agent.

Language: Английский

Citations

48
α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles DOI
Clarice A. D. Caiuby, Matheus Pereira de Jesus, Antonio C. B. Burtoloso

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(11), P. 7433 - 7445

Published: April 28, 2020

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) provide 2-substituted indoles (up 70% yield) just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride dimethylsulfoxonium methylide (23 new examples 45-85% or imino group formation corresponding β-keto anilines presence TiCl4 a Lewis acid (9 33-94% yield).

Language: Английский

Citations

48
Direct Access to 1,1-Dicarbonyl Sulfoxonium Ylides from Aryl Halides or Triflates: Palladium-Catalyzed Carbonylation DOI
Yang Yuan, Xiao‐Feng Wu

Organic Letters, Journal Year: 2019, Volume and Issue: 21(13), P. 5310 - 5314

Published: June 26, 2019

The synthesis of 1,1-dicarbonyl sulfoxonium ylides by palladium-catalyzed carbonylation aryl halides or triflates with α-carbonyl has been developed for the first time. This method provides a general approach to synthetically useful in high efficiency. protocol displays wide substrate scope, showing that resulting have converted into corresponding 1,3-dicarbonyl compounds.

Language: Английский

Citations

44
Visible Light‐Promoted Sulfoxonium Ylides Synthesis from Aryl Diazoacetates and Sulfoxides DOI

Juan Lü,

Lei Li,

Xiang‐Kui He

et al.

Chinese Journal of Chemistry, Journal Year: 2021, Volume and Issue: 39(6), P. 1646 - 1650

Published: Feb. 26, 2021

Main observation and conclusion A visible light‐promoted reaction of donor/acceptor diazoalkanes with sulfoxides towards the synthesis synthetically useful sulfoxonium ylides was reported. The occurred under sole light irradiation without need any transition‐metals or additives, affording corresponding in moderate to good yields. success late‐stage modification natural isolates drug candidates, scale‐up transformation other molecules further rendered approach valuable.

Language: Английский

Citations

34
Copper-catalyzed P–H insertion reactions of sulfoxonium ylides DOI
Xinzhi Zhang, Yangyang Zhang,

Cuijian Liang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(26), P. 5767 - 5771

Published: Jan. 1, 2021

A copper-catalyzed P–H insertion reaction between sulfoxonium ylides and H-phosphorus oxides has been developed to synthesize α-phosphonyl carboxylate derivatives.

Language: Английский

Citations

33
Elemental Sulfur-Mediated Synthesis of Quinoxalines from Sulfoxonium Ylides DOI

Trayambek Nath Chaubey,

Paran J. Borpatra, Satyendra Kumar Pandey

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5329 - 5332

Published: July 7, 2023

A novel straightforward and catalyst-free approach for synthesizing quinoxaline derivatives from sulfoxonium ylides o-phenylenediamines mediated by elemental sulfur has been described. Due to the simple mild reaction conditions, decorated with different functional groups furnished moderate high yields of were well tolerated. Finally, large-scale reactions, synthesis pyrazines, some bioactive compounds are used illustrate potential utility developed approach.

Language: Английский

Citations

14
Synthesis of isoxazolidines via catalyst-free one-pot three-component cycloaddition of sulfoxonium ylides, nitrosoarenes and alkenes DOI
Xing Li,

Pingan Zhai,

Yongsheng Fang

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(5), P. 988 - 995

Published: Jan. 1, 2021

A general and practical strategy for the construction of various keto-substituted isoxazolidines via one-pot three-component reaction easily accessible, safer more stable sulfoxonium ylides, nitrosoarenes olefins is described.

Language: Английский

Citations

28