Electrochemical α-C(sp3)–H/N–H Cross-Coupling of Isochromans and Azoles DOI Creative Commons
Guoping Li, Bing Yan, Liangliang Wu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 30(1), P. 4 - 4

Published: Dec. 24, 2024

Isochroman and azole moieties are both present in a wide variety of biologically active molecules. Their efficient combination under mild reaction conditions is beneficial for obtaining small-molecule drug candidates. In this paper, we describe electrochemical α-C(sp3)–H/N–H cross-coupling reactions between isochromans azoles, yielding products moderate to excellent yields. This protocol does not require any catalysts or exogenous oxidants can be performed at room temperature air. Control experiments cyclic voltammetry showed that the may proceed through radical coupling nucleophilic addition processes.

Language: Английский

Paired Electrolysis-Enabled Arylation of Quinoxalin-2(1H)-ones DOI

Jia-Cheng Hou,

Jun Jiang,

Yan-Cui Wen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6117 - 6125

Published: April 24, 2024

The first paired electrolysis-enabled arylation of quinoxalin-2(1H)-ones was achieved using cyanoarenes as the reagents. A variety 3-arylquinoxalin-2(1H)-ones with various important functional groups were obtained in moderate to good yields under metal- and chemical oxidant-free conditions. With a pair reductive oxidative processes occurring among substrates reaction intermediates, power consumption can be dramatically reduced.

Language: Английский

Citations

22

Electrochemical Oxidative Annulation of Inactivated Alkynes for the Synthesis of Sulfonated 2H-Chromene Derivatives DOI

Jagadeesh Reddy Thondur,

Duddu S. Sharada, Gedu Satyanarayana

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(16), P. 2793 - 2797

Published: April 18, 2023

A unique, facile, and straightforward electrochemical oxidative annulation of inactivated propargyl aryl ethers with sulfonyl hydrazides leading to 3-sulfonated 2H-chromenes has been achieved. Significantly, this protocol involves a green approach that works under mild reaction conditions using constant current in an undivided cell is devoid oxidants catalysts. Notably, the process exhibited broad scope functional group tolerance deliver would represent alternative sustainable strategy versus conventional chromene synthesis.

Language: Английский

Citations

16

Organo-electroreduction enables arylcarboxylation of styrenes DOI
Yanwei Wang, Qian Wang, Zile Zhu

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 27, 2024

Language: Английский

Citations

6

Electrifying synthesis of organosilicon compounds – from electrosynthesis to electrocatalysis DOI Creative Commons
Krzysztof Kuciński

Inorganic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(5), P. 1382 - 1394

Published: Jan. 1, 2023

Organosilicon compounds via electrosynthesis – the recent developments and further challenges.

Language: Английский

Citations

11

Electrophotocatalytic Tellurosulfonylation of Alkynes for the Synthesis of β-(Telluro)vinyl Sulfones DOI

Zhiheng Zhao,

Huiping Zhang, Hongyan Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6114 - 6119

Published: July 5, 2024

Difunctionalization of alkynes has gained a lot interest in current organic chemistry. Herein, we developed an electrophotocatalytic multicomponent cascade reaction and indoles with sulfinic acid sodium salts using elemental tellurium as the source. Using synergistic anodic oxidation visible-light irradiation, various β-(telluro)vinyl sulfones have been prepared. This strategy features mild conditions, excellent substrate scope, readily available starting materials, great functional group tolerance.

Language: Английский

Citations

4

Green Synthesis of 1,4-Dihydropyridines through Catalyst-Free Multicomponent Hantzsch Reaction in an Undergraduate Teaching Laboratory DOI
Yan Zhang,

Xiuya Ma,

Xinyu Zhou

et al.

Journal of Chemical Education, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 27, 2025

Multicomponent reactions (MCRs) are fascinating chemical processes where three or more starting materials come together to form a single product. By exploring various MCRs, second-year undergraduate students learn about the synergy between different functional groups and how they influence reactivity, power of streamlined approach compared conventional stepwise reactions, critical thinking MCR mechanisms. Herein, we introduce valuable synthetic method for constructing heterocyclic compounds through multiple-component condensation/cycloaddition process. Specifically, focus on 1,4-dihydropyridine (1,4-DHP), privileged N-heterocyclic scaffold widely used in medicinal chemistry, particularly 4-aryl-3,5-dicarboxylated derivatives. The experiment provides an excellent opportunity explore concept green chemistry while synthesizing structurally interesting useful molecules using readily available materials. achieve this condensation reaction 2-furaldehyde (furfural), acetoacetic acid tert-butyl ester, ammonium acetate. Key features teaching include following. (1) reaction: involves concise, multicomponent with short time. (2) Catalyst-free: Notably, proceeds without need solvents catalysts. (3) Visually striking system: change system is visually evident, enhancing learning experience. (4) Useful methodology drug synthesis: has practical implications synthesis. We successfully implemented proposal across five parallel student groups, involving approximately 150 participants. experimental procedures encompass organic synthesis, thin-layer chromatography (TLC), nuclear magnetic resonance (NMR) analysis.

Language: Английский

Citations

0

Radical 1,2-fluoroalkylation/stannylation of terminal alkynes DOI
Vyacheslav I. Supranovich, Alexander D. Dilman

Journal of Fluorine Chemistry, Journal Year: 2025, Volume and Issue: 283-284, P. 110422 - 110422

Published: March 23, 2025

Language: Английский

Citations

0

Electrochemical synthesis of 2-alkyl-4-phenylalkan-2-ols via cathodic reductive coupling of alkynes with unactivated aliphatic ketones DOI

Anil Balajirao Dapkekar,

Gedu Satyanarayana

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(20), P. 2915 - 2918

Published: Jan. 1, 2023

Herein, we present an efficient electrochemical method for synthesizing 2-alkyl-4-phenylalkan-2-ols through electrochemically driven cathodic reductive coupling of the terminal and internal acetylenes with unactivated aliphatic ketones under mild conditions. The process proceeds a ketyl radical, which then activates aryl acetylene causes complete reduction triple bond moiety. This strategy is environmentally benign exhibits broad substrate scope ubiquitously available starting materials.

Language: Английский

Citations

8

Stereoselective Fluoroalkylacylation of Alkynes via Cooperative N-Heterocyclic Carbene/Palladium Catalysis DOI
Ying Huang,

Xin-Han Wang,

Chun-Lin Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(16), P. 3441 - 3446

Published: April 16, 2024

Herein, a cooperative N-heterocyclic carbene- and palladium-catalyzed three-component reaction of alkynes with aldehydes fluoroalkyl iodides is developed. A series biologically valuable CF2R-incorporated α-substituted enones was obtained in moderate to good yields. This mild catalytic method exhibits exclusive regio- stereoselectivity, excellent functional group tolerance, broad substrate scope including terminal internal alkynes. Mechanistic investigations disclose that this alkyne fluoroalkylacylation proceeds via radical relay process which vinyl serve as putative intermediates.

Language: Английский

Citations

3

Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters DOI Creative Commons
Pu Chen, Huawen Huang,

Qi Tan

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(6), P. 2667 - 2667

Published: March 15, 2023

The synthetic strategies of oxime derivatives participating in radical-type reactions have been rapidly developed the last few decades. Among them, N–O bond cleavage esters leading to formation nitrogen-centered radicals triggers adjacent C–C produce carbon-centered free radicals, which has virtually used organic synthesis recent years. Herein, we summarized radical involving and through this special reaction form, including those from acyl ester cyclic ketoxime derivatives. These contents were systematically classified according different types. In review, after 2021 included, with emphasis on substrate scope mechanism.

Language: Английский

Citations

6