Multicomponent Reaction of CS2, Amines, and Sulfoxonium Ylides in Water: Straightforward Access to β-Keto Dithiocarbamates, Thiazolidine-2-thiones, and Thiazole-2-thiones DOI
Naveen Kumar, Ajay Sharma, Upendra Kumar

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 6120 - 6125

Published: April 5, 2023

Simple, versatile, and catalyst-free synthetic methods for β-keto dithiocarbamates, thiazolidine-2-thiones, thiazole-2-thiones via the multicomponent reaction of CS2, amines, sulfoxonium ylides have been described. The furnished dithiocarbamates in presence CS2 secondary whereas primary amines afforded thiazolidine-2-thiones or after dehydration an acidic environment. With simple procedures, has a wide substrate scope excellent functional group tolerance.

Language: Английский

Asymmetric transformations from sulfoxonium ylides DOI Creative Commons
Clarice A. D. Caiuby, Lucas G. Furniel, Antonio C. B. Burtoloso

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 13(5), P. 1192 - 1209

Published: Dec. 8, 2021

Sulfoxonium ylides are important surrogates for diazo compounds, and their use in industry as safer alternatives has been evaluated during recent years. Beyond the known classical transformations, these have also used a surprising plethora of novel intrinsic chemical reactions, especially Bench stability handling an advantage this class organosulfur molecules. Despite this, efficient asymmetric specifically catalytic enantioselective versions, only recently reported, there specific reasons this. This perspective article covers topic from first studies up to latest advances, giving personal perspectives showing main challenges area coming

Language: Английский

Citations

94
Synthesis and applications of thiosulfonates and selenosulfonates as free-radical reagents DOI Creative Commons
Xin Wang, Jianping Meng, Dongyang Zhao

et al.

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 34(4), P. 107736 - 107736

Published: Aug. 11, 2022

Language: Английский

Citations

61
Recent advances in the synthesis and applications of β-keto sulfones: new prospects for the synthesis of β-keto thiosulfones DOI
Raju Jannapu Reddy,

Arram Haritha Kumari,

Jangam Jagadesh Kumar

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(14), P. 3087 - 3118

Published: Jan. 1, 2021

This review highlights recent developments relating to the preparation of β-keto sulfones and thiosulfones. And, also focused on widespread synthetic applications for assembling many valuable carbo- heterocycles.

Language: Английский

Citations

60
Transition-Metal-, Additive-, and Solvent-Free [3 + 3] Annulation of RCF2-Imidoyl Sulfoxonium Ylides with Cyclopropenones to Give Multifunctionalized CF3-Pyridones DOI

Si Wen,

Yanhui Chen,

Qingyu Tian

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 87(2), P. 1124 - 1132

Published: Dec. 29, 2021

An efficient and practical strategy was developed to synthesize 1,3,4-triaryl-6-trifluoromethylpyridones from CF3-imidoyl sulfoxonium ylides cyclopropenones in good excellent yields. This stepwise [3 + 3] annulation reaction carried out under transition-metal-, additive-, solvent-free conditions, generating 1 equiv of dimethyl sulfoxide as byproduct tolerating a series functional groups.

Language: Английский

Citations

42
Metal-Free Syntheses of α-Ketothioamide and α-Ketoamide Derivatives from Sulfoxonium Ylides DOI

Trayambek Nath Chaubey,

Paran J. Borpatra, Ajay Sharma

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(43), P. 8062 - 8066

Published: Oct. 24, 2022

An efficient base, additive and metal-free synthetic methods for α-ketothioamide α-ketoamide derivatives from readily available sulfoxonium ylides have been described. Sulfoxonium with primary or secondary amines afforded α-ketothioamides in the presence of elemental sulfur, whereas α-ketoamides were produced when I2 TBHP present. The reaction proceeded well at room temperature generated corresponding molecules good to excellent yields. can be scaled-up tolerated by a range functional groups simple operational procedures.

Language: Английский

Citations

37
Divergent Synthesis of Tetrasubstituted Phenols via [3 + 3] Cycloaddition Reaction of Vinyl Sulfoxonnium Ylides with Cyclopropenones DOI
Shaoyong Chen, Yao‐Fu Zeng,

Wen‐Xuan Zou

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(23), P. 4286 - 4291

Published: June 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.

Language: Английский

Citations

22
Electrochemical Selenylation of Sulfoxonium Ylides for the Synthesis of gem-Diselenides as Antimicrobials against Fungi DOI
Zhongnan Xu,

Jiwen Yao,

Kaihui Zhong

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5572 - 5585

Published: April 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.

Language: Английский

Citations

19
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 DOI

Jiaohang Wei,

Wen‐Xuan Zou,

Qiong Hu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3234 - 3241

Published: Jan. 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.

Language: Английский

Citations

8
Annulation of CF3–Imidoyl Sulfoxonium Ylides with 1,3-Dicarbonyl Compounds: Access to 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles DOI

Si Wen,

Qingyu Tian,

Yanhui Chen

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(19), P. 7407 - 7411

Published: Sept. 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.

Language: Английский

Citations

40
Visible-light-promoted sulfonylation of thiols with aryldiazonium and sodium metabisulphite leading to unsymmetrical thiosulfonates DOI

Yufen Lv,

Jinyun Luo,

Yu-Chuan Ma

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(11), P. 2461 - 2467

Published: Jan. 1, 2021

A facile visible-light-mediated protocol has been proposed for the synthesis of thiosulfonatesviarhodamine 6G catalyzed sulfonylation thiols with aryldiazonium and sodium metabisulphite at room temperature.

Language: Английский

Citations

36