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

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

Catalyst‐Free Synthesis of Thiosulfonates and 3‐Sulfenylindoles from Sodium Sulfinates in Water DOI

Shaoke Li,

Zijun Huang,

Xin Wang

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(32)

Published: April 3, 2024

Abstract This paper presents a green and efficient aqueous‐phase method for the synthesis of thiosulfonates, which has benefits no need catalysts or redox reagents short reaction time, providing with great economic value synthesizing thiosulfonates. Furthermore, 3‐Sulfenylindoles can be easily synthesized using this method, expands potential applications reaction.

Language: Английский

Citations

5

Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C–S Bond Activation DOI

Xuan-Bo Hu,

Yuwei Chen, Chenlong Zhu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13601 - 13607

Published: Sept. 4, 2024

A zinc-mediated cross-electrophile coupling of benzyl sulfonium salts with thiosulfonates via C-S bond cleavage was achieved. The reductive thiolation proceeded well under transition metal-free conditions to afford the desired sulfides in good yields, exhibiting both broad substrate scope and functionality tolerance. In addition, reaction could be applied use selenosulfonate as an effective selenylation agent subjected scale-up synthesis.

Language: Английский

Citations

5

1,n-Thiosulfonylation using thiosulfonates as dual functional reagents DOI
Danhua Ge, Jiawei Chen, Pei Xu

et al.

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 33(11), P. 4732 - 4739

Published: Feb. 15, 2022

Language: Английский

Citations

21

One-pot synthesis of 3-trifluoromethylbenzo[b][1,4]oxazines from CF3-imidoyl sulfoxonium ylides with 2-bromophenols DOI

Mingshi Pan,

Yixin Tong,

Xiaodong Qiu

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(89), P. 12443 - 12446

Published: Jan. 1, 2022

Herein, a method to access 3-trifluoromethyl-1,4-benzoxazines from CF3-imidoyl sulfoxonium ylides and 2-bromophenols has been demonstrated. This synthetic protocol proceeds via one-pot two-step sequence that includes the lithium-bromide-promoted O-H insertion of annulation, merits broad substrate scope, excellent functional tolerance operational simplicity, which provides an alternative means obtaining CF3-substituted heterocycles.

Language: Английский

Citations

20

The thiol-sulfoxonium ylide photo-click reaction for bioconjugation DOI Creative Commons
Chuan Wan,

Zhanfeng Hou,

Dongyan Yang

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 14(3), P. 604 - 612

Published: Dec. 3, 2022

Visible-light-mediated methods were heavily studied as a useful tool for cysteine-selective bio-conjugation; however, many current suffer from bio-incompatible reaction conditions and slow kinetics. To address these challenges, herein, we report transition metal-free thiol-sulfoxonium ylide photo-click that enables bioconjugation under bio-compatible conditions. The is highly generally finished within minutes with naturally occurring riboflavin derivatives organic photocatalysts. catalysts substrates are readily accessible bench stable have satisfactory water solubility. As proof-of-concept study, the was smoothly applied in chemo-proteomic analysis, which provides efficient tools to explore druggable content of human proteome.

Language: Английский

Citations

20

Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process DOI Creative Commons
Yuki Yamamoto, Akiya Ogawa

Molecules, Journal Year: 2023, Volume and Issue: 28(2), P. 787 - 787

Published: Jan. 12, 2023

In recent years, the importance of “environmentally friendly manufacturing” has been increasing toward establishment a resource-recycling society. organic synthesis, as well, it is becoming increasingly important to develop new synthetic strategies with resource conservation and recycling elemental resources in mind, rather than just only synthesis. Many studies on construction frameworks functional molecules using ionic reactions transition-metal-catalyzed have reported, but most them focused formation carbon–carbon bonds. However, essential introduce appropriate groups at positions order for express their functions, furthermore, highly selective preparation multiple considered creation molecules. this review, we focus radical high group selectivity overview progress practical methods simultaneous introduction propose future that emphasize environmental friendliness.

Language: Английский

Citations

11

Straightforward access to α-thiocyanoketones and thiazoles from sulfoxonium ylides DOI
Ajay Sharma,

Ajay Kant Gola,

Satyendra Kumar Pandey

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(68), P. 10247 - 10250

Published: Jan. 1, 2023

Efficient, versatile, and metal-free strategies for synthesizing α-thiocyanoketones thiazoles from β-ketosulfoxonium ylides ammonium thiocyanate have been described. Due to its simplicity, benign reaction conditions, excellent chemoselectivity, high yield, this method represents a unique approach divergent synthesis. Finally, the potential value of developed methods is demonstrated via large-scale reactions synthesis Fanetizole, an anti-inflammatory drug.

Language: Английский

Citations

11

Recent advance: Sulfur ylides in organic synthesis DOI
M. Kumar,

Ifrah Sadaf,

Jyotsna Pamidighantam

et al.

Journal of Heterocyclic Chemistry, Journal Year: 2023, Volume and Issue: 61(1), P. 29 - 70

Published: Oct. 26, 2023

Abstract Sulfur ylides are versatile structures that display various characteristics and participate in a myriad of reactions to produce simple, effective, sometimes stereoselective toward synthesizing sulfur‐containing compounds. Nonetheless, their fulfillment tremendous developments have been made this field the past few decades. In comprehensive review, luminosity is illuminated on application sulfur involved domino, cascade annulation reactions, carbene trapping reagents with chameleonic reactivity. numerous decennary, chemists used solvent‐dependent, rhodium catalyzed, dealkylative intercepted, photochemical reaction, halotrifluoromethylation, benzannulation, amidation name such as Mizoroki–Heck, Suzuki–Miyaura, Sommelet–Hauser rearrangements. Moreover, other prime applications include metal catalysis, epoxidation carbonyl compounds, acylmethylation, cyclomerization, oxidation, insertion reactions. Additionally, some extremely useful play major role synthesis medicinally active heterocycles structural motifs. This review article discusses all these proposed mechanisms, current scenario, at length. tutorial concludes by providing future outlook investigation into compounds synthesized using it great potential be industries, laboratories, pharmaceutical companies, drug production, clinical use, medicinal chemistry, agrochemical purposes.

Language: Английский

Citations

11

Controllable Construction of Vinyl Sulfones and β‐Keto Selenosulfones via Selective Oxidative Sulfonylation of Alkenes DOI
Xiang Liu, Yuan Zhang, Yi Zheng

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(12), P. 1367 - 1372

Published: Feb. 23, 2024

Comprehensive Summary The selective oxidative sulfonylation of alkenes with selenium sulfonate depended on the reaction conditions. electrochemical C—H proceeded smoothly to afford ( E )‐vinyl sulfones good selectivity in an undivided cell without external oxidant. While aerobic trifunctionalization occurred presence KI air, which provides β ‐keto selenosulfones via formation C—O, C—S, and C—Se bonds one‐pot. Following control experiments, a plausible mechanism is proposed rationalize experimental results.

Language: Английский

Citations

4