Synthesis of 4-(trifluoromethyl)thiocoumarins DOI
Alexander S. Golubev, Ivan Golubev,

P. N. Ostapchuk

et al.

Russian Chemical Bulletin, Journal Year: 2024, Volume and Issue: 73(10), P. 3045 - 3054

Published: Oct. 1, 2024

Language: Английский

Efficient Radical‐Mediated Intermolecular α‐Alkylation Reactions of Carbonyl Compounds with Nonactivated Alkenes DOI Creative Commons
Yasuhiro Yamashita, Shu̅ Kobayashi

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(12)

Published: April 27, 2024

Abstract Alkylation reactions are fundamental carbon‐carbon bond‐forming in synthetic organic chemistry. Among them, intermolecular α‐alkylation of carbonyl compounds with alkenes important because they more atom‐economical than the equivalent processes using alkyl halides. However, nonactivated such as 1‐hexene, which can allow use a wide range valuable substrates, have been considered to be very challenging for long time. In this review, radical‐mediated discussed. The examples grouped into three types reactions: peroxide‐mediated reactions, metal‐oxidant‐mediated and photoactivated reactions. Photoredox‐catalyzed alkylation under visible‐light irradiation discussed particularly promising recent hot topic. This review provides brief history new prospects on process α‐carbonyl radical species.

Language: Английский

Citations

5
Divergent photoreduction of nitroaromatic compounds catalysed by dithienoquinoxaline DOI
Zuzana Burešová,

Monika Grygarová,

Eva Prokopová

et al.

Journal of Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 116033 - 116033

Published: Feb. 1, 2025

Language: Английский

Citations

0
Intramolecular and intermolecular benzannulation of arylethanone derivatives enabled by visible light-induced catalytic generation of tether-tunable distonic radical anions DOI

Zhiyou Yu,

Ziye Zhan,

Kang Fu

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel method enables inter-/intramolecular benzannulation to synthesize PAHs have been disclosed. Experimental and DFT data confirm the TDRA's role in HAA step of enolized 1,3-dicarbonyls via asynchronous PCET.

Language: Английский

Citations

0
Visible‐Light‐Mediated [2+2] Photocycloadditions of Alkynes DOI
Qing‐Bao Zhang,

Feng Li,

Bin Pan

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(43)

Published: May 29, 2024

Visible-light-mediated [2+2] photocycloaddition reaction can be considered an ideal solution due to its green and sustainable properties, is one of the most efficient methods synthesize four-membered ring motifs. Although research on alkynes challenging because diminished reactivity alkynes, more significant strain products, remarkable achievements have been made in this field. In article, we highlight recent advances visible-light-mediated reactions with focus mechanism late-stage synthetic applications. Advances obtaining cyclobutenes, azetines, oxetene active intermediates continue breakthroughs fascinating field research.

Language: Английский

Citations

3
Chemodivergent alkylation of trifluoromethyl alkenes via photocatalytic coupling with alkanes DOI Creative Commons
Pol Martínez-Balart, Álvaro Velasco‐Rubio, Sergio Barbeira-Arán

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A photocatalytic methodology for the chemodivergent direct cross-coupling of simple alkanes with trifluoromethyl alkenes that enables selective formation gem -difluoroalkenes and is presented.

Language: Английский

Citations

1
Visible‐Light‐Mediated Activation of Remote C(sp3)−H Bonds by Carbon‐Centered Biradical via Intramolecular 1,5‐ or 1,6‐Hydrogen Atom Transfer DOI

Xintao Gu,

Jiahao Shen,

Ziyu Xu

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(38)

Published: June 21, 2024

Abstract In this study, we introduce a novel intramolecular hydrogen atom transfer (HAT) reaction that efficiently yields azetidine, oxetane, and indoline derivatives through mechanism resembling the carbon analogue of Norrish‐Yang reaction. This process is facilitated by excited triplet‐state carbon‐centered biradicals, enabling 1,5‐HAT suppressing critical 1,4‐biradical intermediates from undergoing Norrish Type II cleavage reaction, pioneering unprecedented 1,6‐HAT reactions initiated alkenes. We demonstrate synthetic utility compatibility method across various functional groups, validated scope evaluation, large‐scale synthesis, derivatization. Our findings are supported control experiments, deuterium labeling, kinetic studies, cyclic voltammetry, Stern–Volmer density theory (DFT) calculations.

Language: Английский

Citations

0
Visible‐Light‐Mediated Activation of Remote C(sp3)‐H Bonds by Carbon‐Centered Biradical via Intramolecular 1,5‐ or 1,6‐Hydrogen Atom Transfer DOI

Xintao Gu,

Jiahao Shen,

Ziyu Xu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(38)

Published: June 21, 2024

In this study, we introduce a novel intramolecular hydrogen atom transfer (HAT) reaction that efficiently yields azetidine, oxetane, and indoline derivatives through mechanism resembling the carbon analogue of Norrish-Yang reaction. This process is facilitated by excited triplet-state carbon-centered biradicals, enabling 1,5-HAT suppressing critical 1,4-biradical intermediates from undergoing Norrish Type II cleavage reaction, pioneering unprecedented 1,6-HAT reactions initiated alkenes. We demonstrate synthetic utility compatibility method across various functional groups, validated scope evaluation, large-scale synthesis, derivatization. Our findings are supported control experiments, deuterium labeling, kinetic studies, cyclic voltammetry, Stern-Volmer density theory (DFT) calculations.

Language: Английский

Citations

0
Visible-light-induced selective hydrolipocyclization and silylation of alkenes: access to ring-fused quinazolin-4(3H)-ones and their silicon-substituted derivatives DOI
Shoucai Wang, Ziren Chen, Fei Xue

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(21), P. 6019 - 6025

Published: Jan. 1, 2024

A visible-light-induced intermolecular silylation and hydrolipocyclization using hydrosilane as the hydrogen silicon source has been developed, which provided an efficient pathway for synthesis of organosilanes polycyclic quinazolinones.

Language: Английский

Citations

0
Photo-Induced Pyridylic C(sp3)–H Alkylation with Unactivated Alkenes Enabled by Hydrogen Atom Transfer/Lewis Acid Cocatalysis DOI
Yusuke Kuroda, Hikaru Saito,

Tsukasa Tawatari

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(20), P. 15036 - 15042

Published: Sept. 27, 2024

Language: Английский

Citations

0
Radical pathways for 2,4-chromandione synthesis via photoexcitation of 4-hydroxycoumarins DOI Creative Commons
Sumitava Mallik,

Enrico Sfreddo,

Hailong Wang

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

4-Hydroxycoumarins are well-known for their ground-state nucleophilic behavior, which has been widely exploited functionalization. Herein, we reveal a previously unexplored photochemical reactivity: upon deprotonation and excitation with purple light, 3-substituted 4-hydroxycoumarins reach an excited state act as single-electron transfer (SET) reductants, generating radicals from stable substrates. This newfound reactivity enables the direct synthesis of 3,3-disubstituted 2,4-chromandiones

Language: Английский

Citations

0