Visible‐Light‐Induced Synthesis of Thioethers through Three‐Component Reactions of α‐Diazoesters, Thiols, and Cyclic Ethers DOI

Yufen Lv,

Zhiwei Wang,

Jindong Hao

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(8)

Published: June 26, 2023

Abstract Thioethers are important sulfur‐containing compounds that have widespread application in organic synthesis, medicinal chemistry and materials science. Herein, a visible‐light‐mediated three‐component reaction of α‐diazoester, thiol, cyclic ether leading to thioether has been developed at room temperature. Through this methodology, variety coupling products with the introduction ring‐opening could be efficiently assembled under photocatalyst‐ additive‐free conditions.

Language: Английский

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors DOI
Ziyan Zhang, Vladimir Gevorgyan

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

Citations

67

Visible light-mediated photolysis of organic molecules: the case study of diazo compounds DOI
Rafael D. C. Gallo, Guilherme Cariello Silva, Tales A. C. Goulart

et al.

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

Citations

48

Photocatalyst-free visible-light-mediated three-component reaction of α-diazoesters, cyclic ethers and NaSCN to access organic thiocyanates DOI

Zhiwei Wang,

Na Meng,

Yufen Lv

et al.

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 34(2), P. 107599 - 107599

Published: June 13, 2022

Language: Английский

Citations

59

Visible photons as ideal reagents for the activation of coloured organic compounds DOI Creative Commons
Lorenzo Di Terlizzi, Luca Nicchio,

Stefano Protti

et al.

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

Citations

13

Dark and Light Reactions of Carbenes─Merging Carbene Transfer Reactions with N-Heterocyclic Carbene Catalysis for the Synthesis of Hydroxamic Acid Esters DOI
Bao‐Gui Cai, Qian Li, Claire Empel

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(18), P. 11129 - 11136

Published: Aug. 30, 2022

Herein, we report visible light and N-heterocyclic carbene (NHC) jointly promoted multicomponent transfer reactions. Under the optimized reaction conditions, two kinds of important hydroxamic acid esters were obtained in good yields depending on media used. The key to this success was driven by blue light-promoted generation free species fast situ formation under NHC-catalyzed conditions. mild excellent functional group tolerance, useful synthetic transformations, successful modification natural products drug molecules proved utility practicality method.

Language: Английский

Citations

29

Visible-Light-Induced Imide Synthesis through a Nitrile Ylide Formation/Trapping Cascade DOI
Bao‐Gui Cai,

Wei‐Zhong Yao,

Lei Li

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(36), P. 6647 - 6652

Published: Sept. 2, 2022

A visible-light-promoted three component reaction of diazo compounds, nitriles, and carboxylic acids is reported. The utilizes acceptor-only compounds as carbene precursors nitriles carbene-trapping reagents to form the key nitrile ylides. Under optimal conditions, a wide range imide products were obtained in good excellent yields. gram-scale synthesis synthetic application isoquinoline-1,3(2H,4H)-dione derivatives further proved value this method.

Language: Английский

Citations

21

Photochemical multicomponent transformation of acceptor-only diazoalkanes by merging their cycloaddition and carbene reactivities DOI
Bao‐Gui Cai, Guoyong Xu, Jun Xuan

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 34(9), P. 108335 - 108335

Published: March 15, 2023

Language: Английский

Citations

13

Synthesis of functionalized S-benzyl dithiocarbamates from diazo-compounds via multi-component reactions with carbon disulfide and secondary amines DOI
Nitin Kumar, Rapelly Venkatesh, Jeyakumar Kandasamy

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(34), P. 6766 - 6770

Published: Jan. 1, 2022

Triflic acid promoted multicomponent synthesis of functionalized S -benzyl dithiocarbamates from diazo compounds and secondary amines in the presence carbon disulfide is described.

Language: Английский

Citations

16

Visible-Light-Initiated Multicomponent Reactions of α-Diazoesters to Access Organophosphorus Compounds DOI

Chengming Qu,

Jindong Hao,

Hongyu Ding

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(19), P. 12921 - 12931

Published: Sept. 21, 2022

A simple visible-light-initiated strategy has been established for the construction of organophosphorus compounds via aerobic multicomponent reaction α-diazoesters, cyclic ethers, and P(O)H under air. number phosphonates phosphinates could be efficiently isolated in moderate to good yields without use photosensitizers metal reagents. This advantages mild condition, operation, eco-friendly energy, functional-group tolerance, gram-scale synthesis.

Language: Английский

Citations

16

Visible-light-mediated multi-component carbene transfer reactions of α-diazoesters to construct multisubstituted pyrazoles and 1,3-dicarbonyl derivatives DOI

Hongyu Ding,

Zhiwei Wang,

Chengming Qu

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(20), P. 5530 - 5535

Published: Jan. 1, 2022

A visible-light-promoted strategy has been developed for the assembly of multisubstituted pyrazoles and 1,3-dicarbonyl derivatives via a multi-component carbene transfer reaction α-diazoesters.

Language: Английский

Citations

15