Recent Developments in C‐S, C‐Se Bond Formation via Three‐Component Reactions of Alkynes DOI Open Access
Zhan‐Yong Wang, Guipeng Feng, Xiaoying Jiang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(46)

Published: Aug. 28, 2024

Abstract Alkynes are valuable building blocks in organic synthesis. They can undergo three‐component difunctionalization to create sulfur or selenium‐containing compounds. Three‐component reactions of alkynes atom economic, practical and regioselective. This review will disscuss decade developments, including C−S C−Se bond formation via thiolation, sulfonylation selenylation. Recent developments be mainly categorized into three types. (1) Radical C−S/S−Se is a hot topic. Reactions initiated by S/Se radicals other exhibit two types selectivities. Photochemical electrochemical under eco‐friendly conditions have been increasingly reported. (2) Some transformations involve electrophilic three‐membered ring intermediates. Thiiraniums, seleniraniums, iodoniums among the most prevalent species. ring‐opening various nucleophiles participate tandem reactions. (3) Metal‐catalyzed reactions, classic category, also discussed text. In following section, we provide an overview based on mechanisms substrates. The roles added reagents discussed.

Language: Английский

Photoelectrochemical upcycling of PVC plastic waste for the synthesis of chlorinated quinolinone derivatives DOI
Kai Zheng, Jingwen He, Zhang Li-xi

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Herein, an environmentally friendly methodology has been established for the photoelectrochemical chlorination of C(sp 2 )–H bonds in quinolinone derivatives using PVC plastic waste as chlorine source.

Language: Английский

Citations

3

Electrochemical Enaminone-Thioamide Annulation and Thioamide Dimeric Annulation for the Tunable Synthesis of Thiazoles and 1,2,4-Thiadiazole DOI

Qihui Huang,

Jianchao Liu, Jie‐Ping Wan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(25), P. 5263 - 5268

Published: June 14, 2024

A green and sustainable electrochemical oxidative cyclization of enaminones with thioamides under metal- oxidant-free conditions has been developed, providing an efficient approach for thiazole synthesis. Furthermore, 1,2,4-thiadiazoles can be selectively accessed via the dimerization in absence enaminones.

Language: Английский

Citations

18

Regioselective electrochemical cascade C–H sulfonylation–bromination of indolizines to access difunctionalized indolizines DOI
Wenxuan Jiang, Xiang Liu, Chuanying Zhu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(8), P. 2306 - 2312

Published: Jan. 1, 2024

Regioselective electrochemical C–H sulfonylation–bromination between indolizines, sodium sulfinates, and KBr has been established in an undivided cell, which serves as both the brominating agent electrolyte.

Language: Английский

Citations

8

Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides DOI
Zhixian Yang,

Lu-Cai Ding,

Gui-Hong Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10660 - 10677

Published: July 18, 2024

Two general protocols for the regioselective electrochemically enabled sulfonylation cyclization of

Language: Английский

Citations

8

Recent progress in the organoselenium-catalyzed difunctionalization of alkenes DOI
Pei Qu, Gong‐Qing Liu

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Selenium-based catalysts have recently been utilized to facilitate a variety of new organic transformations, owing their intrinsic advantages, including low cost, toxicity, stability in both air and water, strong compatibility with diverse functional groups. The difunctionalization alkenes-the process incorporating two groups onto carbon-carbon double bond-has garnered particular interest within the chemical community its significant applications synthesis. Recently, organoselenium-catalyzed alkenes has emerged as an ideal powerful route obtain high-value vicinal difunctionalized molecules. This review emphasizes recent advancements this rapidly evolving field, focusing on scope, limitations, mechanisms various reactions.

Language: Английский

Citations

1

Recent advances in multicomponent synthesis of pyrazoles DOI
Jing Zhou,

Quan‐Quan Zhou,

Jie‐Ping Wan

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Pyrazole moiety is considered as an important N-heterocycle in pharmaceuticals and many other functional molecules. The utilization of multicomponent reaction a major tool the current approaches pyrazole synthesis. Considering power significance synthesis, we review herein latest developments this field. According to typical features, contents are divided into reactions with different NN fragment sources, such hydrazine, hydrazone, amidine, nitrile, diazo compounds, ring construction, covering works published since 2019 date.

Language: Английский

Citations

6

Electricity-driven, oxidative C–H selenylative and tellurylative annulation of N-(2-alkynyl)anilines: sustainable synthesis of 3-selanyl/tellanylquinolines DOI Creative Commons

Ainala Naresh,

H. Sai Keerthana,

Nilanjana Mukherjee

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(55), P. 7057 - 7060

Published: Jan. 1, 2024

A metal- and oxidant-free, electricity-driven C–H selenylative tellurylative annulation of N -(2-alkynyl)anilines with diorganyl dichalcogenides is developed to access 3-chalcogenylquinolines.

Language: Английский

Citations

5

Electrochemical Annulation of p-Alkoxy or p-Hydroxy Anilines with Enaminones for Selective Indole and Benzofuran Synthesis DOI

Zukang Zhong,

Yunyun Liu, Lihua Liao

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 11, 2025

The green and sustainable electrochemical oxidative cyclization of enaminones with p-methoxy/p-hydroxy anilines has been developed, enabling the regioselective synthesis indoles benzofurans. methods are significant advantage not only due to mild metal-free conditions, but also because employment easily available stable aniline substrates replace unstable quinoneimide for a similar annulation in previous work.

Language: Английский

Citations

0

Synthesis of 5‐Arylselenyluracils via Bromide‐Catalyzed Selective C(sp2)‐H Selenylation of Uracils DOI

Zhouting Zeng,

Feng Zhao, Huaixin Wei

et al.

Asian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 28, 2025

Abstract Herein, an efficient method for the synthesis of 5‐arylselenyluracils via bromide‐catalyzed selective C( sp 2 )‐H selenylation uracils using boronic acid and elemental selenium as selenyl source was successfully developed. This proceeded smoothly a series arylboronic acids under metal‐free strong oxidant‐free conditions. protocol offered simple catalytic conditions, high efficiency, good functional group compatibility, easy operation, scalable. Furthermore, mechanistic studies suggested that this transformation possibly undergone radical pathway.

Language: Английский

Citations

0

Electrocatalytic Cleavage of C–C Bonds in Lignin Models Using Nonmetallic Catalysts at Ambient Conditions DOI Creative Commons

Guangyong Liu,

Ziqi Zhai,

Yumiao Lu

et al.

Chem & Bio Engineering, Journal Year: 2024, Volume and Issue: 1(4), P. 357 - 365

Published: Feb. 26, 2024

Lignin, characterized by its amorphous, heavily polymerized structure, is a primary natural source of aromatic compounds, yet complex constitution poses considerable challenges in transformation and utilization. Therefore, the selective cleavage C-C bonds represents critical challenging step lignin degradation, essential for production high-value compounds. In this study, we report simple electrocatalytic approach valorization via bond developing nonmetallic electrocatalyst carbon-based materials. It found that hydrophilicity hydrophobicity have significant effect on degradation process. Under mild conditions, hydrophilic carbon paper exhibits 100% substrate conversion, yielding 97% benzaldehyde 96% quinone with ionic liquid electrolytes. The mechanism study shows catalyst higher surface defects favors electron transfer oxidative process bonds. These results signify substantial advancement offering an environmentally friendly, metal-free electrochemical route.

Language: Английский

Citations

2