Synthesis of naphtho[1,2-b]furan-2-carbaldehydes and naphtho[2,1-b]furan-2-carbaldehydes via electrocatalytic 3,3-rearrangement/cyclization of propargylic aryl ethers under mild conditions DOI Creative Commons

Kaili Cen,

Mixia Ouyang,

Guojun He

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: June 1, 2024

An electrocatalytic 3,3-rearrangement/cyclization approach has been developed for the transformation of aryl-substituted propargylic aryl ethers to naphtho[1,2-b]furan-2-carbaldehyde and naphtho[2,1-b]furan-2-carbaldehyde derivatives. The reaction proceeded efficiently under mild conditions in absence metal- chemical-oxidant, yielding desired products with good substrate scope functional group tolerance via a radical pathway. Furthermore, control experiment revealed that phenylselenyl-substituted secondary alcohol might be intermediate, 18O labeling indicated oxygen source product possibly deriving from water. Significantly, further transformations were conducted showcase utility this electrosynthesis strategy.

Language: Английский

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

17

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

2

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

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

7

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

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

0

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

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

A Practical Electrochemical Approach for Synthesizing Selenyl-Dihydrobenzofurans and Chromane with a Tetrasubstituted Carbon Center DOI
Xianqiang Kong, Xiaohong Chen, Zhong‐Yan Cao

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(17), P. 2695 - 2702

Published: June 24, 2024

Abstract A straightforward and efficient electrochemical method for the anodic oxidative selenenylation of 2-(2-arylallyl)phenols a 2-(3-arylbut-3-en-1-yl)phenol with diselenides under ambient air conditions has been outlined. This allows synthesis selenyl-dihydrobenzofurans chromane featuring sterically hindered tetrasubstituted carbon center, demonstrated through 25 examples yields reaching up to 98%. Initial mechanistic investigations suggest likely participation pivotal seleniranium cation species in regulating reactivity.

Language: Английский

Citations

2