Visible Light-Induced Reactions of Diazo Compounds and Their Precursors

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(11), P. 7214 - 7261

Published: May 16, 2024

In recent years, visible light-induced reactions of diazo compounds have attracted increasing attention in organic synthesis, leading to improvement existing reactions, as well the discovery unprecedented transformations. Thus, photochemical or photocatalytic generation both carbenes and radicals provide milder tools toward these key intermediates for many valuable However, vast majority transformations represent new reactivity modes compounds, which are achieved by decomposition photoredox catalysis. particular, use a redox-active photocatalysts opens avenue plethora radical reactions. The application methods led inaccessible classical associated with metal carbenes. most cases, act sources but can also serve acceptors. Importantly, described processes operate under mild, practical conditions. This Review describes this subfield compound chemistry, particularly focusing on advancements.

Language: Английский

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Visible light-mediated photolysis of organic molecules: the case study of diazo compounds

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(48), P. 7346 - 7360

Published: Jan. 1, 2023

This article discusses the photochemistry of several diazo compounds undergoing visible light-mediated photolysis to generate free carbenes (or other highly reactive intermediates), which can be sequentially trapped by different reacting partners.

Language: Английский

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Visible photons as ideal reagents for the activation of coloured organic compounds

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(10), P. 4926 - 4975

Published: Jan. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Language: Английский

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Base-catalyzed stereoselective thiosulfonylation of ynones for the facile synthesis of thio-functionalized vinyl sulfones

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(5), P. 1224 - 1229

Published: Jan. 1, 2023

Brønsted base catalyzed thiosulfonylation and trifluoromethylthiosulfonylation of ynones produced thio-functionalized vinyl sulfones in high yields with excellent E -selectivity.

Language: Английский

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Electrochemical Difunctionalization of Alkenes: Simultaneous Construction of C–Se and C–S Bonds

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5321 - 5328

Published: April 10, 2023

Electrochemical oxidation of alkene difunctionalization with simultaneous construction C-Se and C-S bonds is reported. The products β-selenylethyl dithiocarbamates are obtained CS2, amines, alkenes, diphenyl diselenides in the absence any oxidant or metal. Furthermore, transformation compatible various groups. In preliminary mechanism studies, we propose three possible pathways.

Language: Английский

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Direct C−H Sulfuration: Synthesis of Disulfides, Dithiocarbamates, Xanthates, Thiocarbamates and Thiocarbonates

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(9)

Published: Feb. 29, 2024

Abstract In light of the important biological activities and widespread applications organic disulfides, dithiocarbamates, xanthates, thiocarbamates thiocarbonates, continual persuit efficient methods for their synthesis remains crucial. Traditionally, preparation such compounds heavily relied on intricate multi‐step syntheses use highly prefunctionalized starting materials. Over past two decades, direct sulfuration C−H bonds has evolved into a straightforward, atom‐ step‐economical method organosulfur compounds. This review aims to provide an up‐to‐date discussion disulfuration, dithiocarbamation, xanthylation, thiocarbamation thiocarbonation, with special focus describing scopes mechanistic aspects. Moreover, synthetic limitations some these methodologies, along key unsolved challenges be addressed in future are also discussed. The majority examples covered this accomplished via metal‐free, photochemical or electrochemical approaches, which alignment overraching objectives green sustainable chemistry. comprehensive consolidate recent advancements, providing valuable insights dynamic landscape strategies crucial classes

Language: Английский

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Electro-Oxidative Three-Component Synthesis of 3,5-Disubstituted-1,2,4-Thiadiazoles from Amines, Amidines, and CS₂

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

Published: March 29, 2025

1,2,4-Thiadiazoles, a significant class of heterocyclic compounds, are widely found in biologically active molecules. Herein, we report green electrochemical three-component reaction amines, amidines, and CS2 for the effective synthesis 3,5-disubstituted-1,2,4-thiadiazoles under metal- oxidant-free conditions. Both aliphatic aryl amines well-tolerated at room temperature simple undivided cell. A series 1,2,4-thiadiazoles prepared with excellent functional groups.

Language: Английский

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Catalyst- and additive-free syntheses of rhodanine andS-alkyl dithiocarbamate derivatives from sulfoxonium ylides

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(11), P. 1509 - 1512

Published: Jan. 1, 2023

An efficient catalyst- and additive-free facile access to rhodanine S -alkyl dithiocarbamate derivatives via multi-component reaction of amines, CS 2 α-ester sulfoxonium ylides in methanol has been described.

Language: Английский

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Synthesis of 4-Alkylated 1,4-Dihydropyridines: Fe(II)-Mediated Oxidative Cascade Cyclization Reaction of Cyclic Ethers with Enaminones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(16), P. 11627 - 11636

Published: Aug. 9, 2023

Syntheses of highly functionalized 4-alkylated 1,4-dihydropyridines (1,4-DHPs) from cyclic ethers and enaminones via iron(II)-mediated oxidative free radical cascade C(sp3)-H bond functionalization/C(sp3)-O cleavage/cyclization reaction have been first developed. This novel synthetic strategy offers an alternative method for the construction 1,4-DHPs by using esters as C4 sources, well expands application in heterocycle synthesis.

Language: Английский

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Brønsted base-catalyzed assembly of sulfochromeno[4,3-b]pyrrolidines via tandem [3 + 2] cycloaddition–SuFEx click reaction of ethenesulfonyl fluorides and o-hydroxyaryl azomethines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(21), P. 6177 - 6183

Published: Jan. 1, 2024

o -Hydroxyaryl azomethine ylides react with ethenesulfonyl fluorides via a tandem [3 + 2] cycloaddition–SuFEx click process to produce sulfochromeno[4,3- b ]pyrrolidines in high yields.

Language: Английский

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