Visible-light-promoted selenylation/cyclization of o-(1-alkynyl) benzoates to access seleno-substituted isocoumarins DOI

Mei-Lin Ren,

Xi-Rui Gong,

Yanyan Chen

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(36), P. 7327 - 7331

Published: Jan. 1, 2024

A simple and efficient method to access 4-selenyl-isocoumarin derivatives through visible-light-promoted selenylation/cyclization of o -(1-alkynyl) benzoates has been developed.

Language: Английский

Photocatalytic C–P bond formation based on the reaction of carbon-centered radicals with phosphides DOI

Shiyi Zhao,

Yi-Yun Huang,

Shihao Deng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4882 - 4894

Published: Jan. 1, 2024

This review focuses on the synthesis of C–P bonds using carbon-centered radicals with phosphorous compounds different valence states (P III , P V 4 ) under photocatalysis.

Language: Английский

Citations

6

Photoredox catalysis of acridinium and quinolinium ion derivatives DOI
Shunichi Fukuzumi, Yong‐Min Lee, Wonwoo Nam

et al.

Bulletin of the Korean Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 9, 2024

Abstract Photoredox catalysis has attracted increasing attention because of wide range synthetic transformations and solar energy conversion applications. Reviews on photoredox have so far focused predominantly the This review highlights how organic catalysts were developed they function as efficient photocatalysts in mechanistic point views. In particular, 9‐mesityl‐10‐methylactidinium (Acr + –Mes) been highlighted one best catalysts. Acr –Mes was originally a model compound photosynthetic reaction center to mimic long lifetime charge‐separated state which is converted chemical photosynthesis. The reason why acts most catalyst clarified terms one‐electron redox potentials lifetimes electron‐transfer • •+ ) produced upon photoexcitation different solvents. mesityl substituent at 9‐position moiety essential for discussed comparison with acridinium ions substituents R –R) including 10‐methylacridinium ion no (AcrH ). mechanisms are various reactions mimicking quinolinium its derivatives also that –Mes. Finally, immobilization form composite improve catalytic activity stability.

Language: Английский

Citations

3

Cross-Coupling of Carbonyl Derivatives and N-Arylamines Enabled by Visible Light for Easy Access to 1,2-Amino Alcohols DOI
Xu Yan, Hongcheng Zhuang,

Yulin Song

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(2), P. 1078 - 1084

Published: Jan. 7, 2025

We disclosed a new strategy for the synthesis of 1,2-amino alcohols enabled by visible light without requirement photocatalyst and metal. Under irradiation at 400 nm, reaction carbonyl derivatives N-arylamines proceeds via an electron-donor-acceptor (EDA) intermediate, obtaining diverse vicinal amino decorated with two-electron-rich/-deficient aryl group.

Language: Английский

Citations

0

Anticipating Natural Phenolics Through Visible Light‐Induced Photorearrangement of Quinones DOI Creative Commons
Alexander A. Fadeev, Martin Kotora

ChemistryEurope, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 3, 2025

Abstract A general protocol for the photorearrangement of substituted benzo‐ and naphthoquinones using monochromatic blue light irradiation in solution was developed. During this process, quinone ring is transformed into hydroquinone, while substituent undergoes desaturation or annulation onto proximal oxygen formed hydroquinone. We found that preferred acyclic saturated substituents, such as alkyl groups, tendency observed both cyclic unsaturated substituents (allyl, alkenyl, aryl). The diversity participating functional group tolerance transformation allowed us to prepare 10 natural phenolic compounds, suggesting visible may likewise induce their formation from respective quinones sources.

Language: Английский

Citations

0

Photocatalytic and Chemoselective H/D Exchange at α-Thio C(sp3)-H Bonds DOI

Riku Ogasahara,

Miyu Mae,

Yuki Itabashi

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 23, 2025

Deuterated compounds used in drug discovery and live-cell imaging have recently gained the attention of various scientific fields. Although hydrogen-deuterium (H/D) exchange reactions are straightforward deuteration methods, achieving perfect chemoselectivity is challenging. We report highly chemoselective α-thio C(sp3)-H bonds using a thioxanthone or anthraquinone organic photocatalyst bearing an aromatic ketone skeleton D2O as inexpensive deuterium source under 390 nm irradiation. Notably, incorporation at α-positions O/N atoms, benzylic positions, rings was not observed. The present accomplished via single electron transfer mechanism between S-containing substrates, proven by laser-induced time-resolved transient absorption spectroscopic measurements. Furthermore, proposed method could be applied to including pharmaceuticals biologically active with high regioselectivities. available deuterated novel alkylation reagents for future materials Raman were also demonstrated.

Language: Английский

Citations

0

Water Effect on the Photochemistry of Arylazo Sulfonates DOI Creative Commons
Luca Nicchio, Hawraz Ibrahim M. Amin,

Stefano Genualdo

et al.

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

Published: April 30, 2025

The effect of water on visible-light-driven generation aryl radicals or cations from colored shelf-stable arylazo sulfonates has been investigated. Photoinduced ionic and radical decomposition these salts compete, depending the media used. In organic solvents, light-induced homolysis N-S bond occurs, resulting may be used to some extent for arylation reactions. On contrary, in neat water, chemistry is prevented by an efficient photoheterolysis, a reactive cation otherwise generated.

Language: Английский

Citations

0

Recent Advances in Photo-promoted Generalized C3-H Alkylation of Quinoxalin-2(1H)-ones DOI
Youpeng Zuo, Xu Bai, Cong Wang

et al.

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

Published: Jan. 1, 2025

Recent advances in the photo-promoted C3–H alkylation reaction of quinoxalin-2(1 H )-ones with different agents.

Language: Английский

Citations

0

Light-driven Michael addition of indoles to β-nitroolefins in aqueous medium DOI

Periklis X. Kolagkis,

Eirini M. Galathri,

Christoforos G. Kokotos

et al.

Catalysis Today, Journal Year: 2024, Volume and Issue: 441, P. 114868 - 114868

Published: June 5, 2024

Language: Английский

Citations

2

Visible photons for the regioselective nucleophilic ring opening of epoxides DOI Creative Commons

Beatrice Bernardoni,

Lorenzo Di Terlizzi,

Eirini M. Galathri

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(18), P. 9833 - 9839

Published: Jan. 1, 2024

Herein, we introduce a visible-light promoted green, metal-free method for the regioselective nucleophilic ring opening of epoxides by exploiting arylazo sulfones as PhotoAcid Generators (PAGs).

Language: Английский

Citations

1

Base-Mediated Visible-Light-Driven C–H Arylation of Quinoxalin-2(1H)-Ones in Ethanol DOI
Y. Pan,

Luohe Wang,

Yunhong Shi

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(19), P. 14217 - 14227

Published: Sept. 26, 2024

Prior methods for visible-light-driven C-H arylation of quinoxalin-2(1

Language: Английский

Citations

1