Cited by Light-promoted AIBN-catalyzed oxidative cleavage of aryl olefins to aryl ketones

Regulation of Photogenerated Redox Species through High Crystallinity Carbon Nitride for Improved C−S Coupling Reactions DOI

Chen Liu,

Yukun Ma,

Ronghong Lian

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: 17(10)

Published: Jan. 20, 2024

Abstract A novel and efficient approach for the synthesis of α, β‐unsaturated sulfones through heterogeneous photocatalyzed C−S coupling reactions have been developed. The use molten‐salt method derived carbon nitride (MCN), a transition metal‐free polymeric photocatalyst, combined with enhanced crystallinity potassium iodide as an additive, effectively modulates photogenerated reactive redox species, markedly increasing overall reaction selectivity. This achieves shortest time (2 h) high yield (up to 95 %) among reported catalytic bond formation reactions, matching efficiency homogeneous photocatalysts. Furthermore, application challenging alkyne substrates has demonstrated, underscoring potential broad range applications in pharmaceutical research synthetic chemistry.

Language: Английский

Citations

Synergistic insights: electro-organic photocatalysis and nanostructures DOI

Jyoti Bhattacharjee, Subhasis Roy

Chemical Papers, Journal Year: 2024, Volume and Issue: 78(15), P. 8077 - 8105

Published: Aug. 22, 2024

Language: Английский

Citations

KuQuinones: a ten years tale of the new pentacyclic quinoid compound DOI

Francesca Valentini, Federica Sabuzi, Mattia Forchetta

et al.

RSC Advances, Journal Year: 2023, Volume and Issue: 13(13), P. 9065 - 9077

Published: Jan. 1, 2023

KuQuinones: from serendipity synthesis to photo(electro)chemical and biomedical applications.

Language: Английский

Citations

Oxidative transformations of olefins employing persulfate/visible light irradiation in water DOI

Gabriel S. G. Peagno, Airton G. Salles

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(20), P. 4210 - 4215

Published: Jan. 1, 2023

We present a green and economical approach for the photooxidation of diverse olefins through use ammonium persulfate blue light irradiation, resulting in formation vicinal diols from styrenes aliphatic alkenes, vinyl esters diacids α,β-unsaturated ketones. The involvement sulfate radicals reaction medium was established as primary species responsible selective generation products. A significant advantage method lies its broad substrate scope economic feasibility, making it promising alternative to conventional transition metal photocatalysis.

Language: Английский

Citations

Selectively Aerobic Oxidation of Benzylic C—H Bonds Enabled by Dual Anthracene and Cerium Catalysis under Continuous-Flow Conditions^★ DOI

Yuanli Xu, Pan Hui, Yi Yang

et al.

Acta Chimica Sinica, Journal Year: 2023, Volume and Issue: 81(5), P. 435 - 435

Published: Jan. 1, 2023

The benzyl oxidation reaction serves as a crucial functional group transformation method in the field of organic synthesis.Regrettably, traditional reactions frequently necessitate harsh conditions, such elevated temperatures and potent oxidizing agents.In contrast, this article showcases highly selective catalytic benzylic executed within continuous-flow microreactor.By harnessing previously established cerium-alcohol complex's ligand to metal charge transfer (LMCT)-hydrogen atom (HAT) activation mechanism anthracene-cerium synergistic system, diverse array aromatic ketones was synthesized from aryl alkanes with remarkable efficiency under ambient aerobic conditions.The technology, endowed unique advantages heightened illumination efficiency, superior gas-liquid mass transfer, repeatability, scalability, has emerged powerful instrument for scaling-up photocatalytic reactions.In process, flow ethyl acetate solutions comprising Ce(NO3)3•6H2O, tetrabutylammonium bromide (TBABr), 9,10-dibromoanthracene (DBA), trichloroethanol (TCE), ethylbenzene encountered mixed oxygen microreactor.Subsequently, occurred visible light irradiation at room temperature, achieving complete conversion mere 5 min, rapidly generated series good excellent yields.Mechanistic studies indicated paramount importance anthracene-derived catalyst DBA efficiency.Under irradiation, excited state initially oxidatively quenched or peroxide species resulting formation cationic free radical.Subsequently, radical underwent single electron (SET) process low-valent cerium (III) complex, consequently expediting oxidative regeneration (IV) markedly boosting its efficacy.Eventually, efficient system is characterized by simplicity, mild selectivity, minimal waste production, extensive applicability.Furthermore, it effortlessly scalable amenable continuous production.

Language: Английский

Citations

Synthesis of Soluble Quinacridone Photocatalysts for the Homogeneous Oxidation of Thioethers DOI

Mattia Forchetta,

Valerio Baia,

Federica Sabuzi

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(35)

Published: June 25, 2023

Abstract Evaluation of quinacridone (QA) derivatives as homogeneous metal‐free photocatalysts is here presented. QA were synthetized and systematically characterized, measuring their ground state excited redox potentials in dichloromethane (DCM) 1,1,1,3,3,3‐hexafluoro‐2‐propanol (HFIP), order to understand how structural modifications influenced photocatalytic properties. In particular, the effect dicyanomethylene nitro EWG groups was investigated, develop a photocatalyst capable promoting oxidative processes presence molecular oxygen. Among analyzed derivatives, 2,9‐dinitro‐ N,N′ ‐dibutylquinacridone (DNDBQA) one with highest reduction potential (E red* =1.60 V HFIP vs SCE), while N,N’ (DBQA) showed valuable =1.29 V; E ox* =−1.28 making it suitable for bimodal applications reductive processes. Afterwards, examined promote selective aerobic oxidation thioether sulfoxide. Promising results thioanisole achieved all tested photocatalysts, terms yield selectivity. Remarkably, DBQA best performances, catalyzing reaction only 20 minutes, using 0.5 % photocatalyst, showing excellent performances several derivatives.

Language: Английский

Citations

One-Step Electropolymerization of a Dicyanobenzene-Carbazole-Imidazole Dye to Prepare Photoactive Redox Polymer Films DOI

J. Ping Liu,

Octavio Martinez Perez,

Dominic Lavergne

et al.

Polymers, Journal Year: 2023, Volume and Issue: 15(16), P. 3340 - 3340

Published: Aug. 8, 2023

To the best of our knowledge, this study reports first direct electropolymerization a dicyanobenzene-carbazole dye functionalized with an imidazole group to prepare redox- and photoactive porous organic polymer (POP) films in controlled amounts. The POP were grown on indium-doped tin oxide (ITO) carbon surfaces using new monomer, 1-imidazole-2,4,6-tri(carbazol-9-yl)-3,5-dicyanobenzene (1, 3CzImIPN), through simple one-step process. structure activities investigated as photoelectrodes for electrooxidations, heterogeneous photocatalysts photosynthetic olefin isomerizations, solid-state photoluminescence behavior tunable by lithium-ion concentrations solution. results demonstrate that photoredox-POPs can be used efficient photocatalysts, they have potential applications sensing.

Language: Английский

Citations

Synthesis of γ-Undecalactone via Organophotocatalyzed α-C-H Alkylation of 1-Octanol using Continuous-Flow Photoreactors DOI

Meichen Xu,

Yang Xiao, Yi‐Ming Li

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 137, P. 154939 - 154939

Published: Feb. 3, 2024

Language: Английский

Citations

Visible‐light mediated Ugi‐type reaction for the synthesis of 3,3‐disubstituted phthalides DOI

Feiyu Gao,

Chenxin Yin,

Yi He

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2728 - 2734

Published: April 20, 2024

Abstract The synthesis of diverse phthalides containing quaternary carbon centers remains poorly exploited, requiring stepwise reactions with toxic reagents under high temperatures. Herein, we describe a visible‐light promoted, photo‐ and metal‐catalyst‐free protocol for the modular 3,3‐disubstituted water as sole by‐product. This process featured an open‐flask operation three‐component reaction involving isocoumarin self‐photosensitizer aerobic ring contracting rearrangements, allowing convenient preparation 3‐(1′‐indolyl)‐phthalides in moderate to good yields. mechanistic investigations suggested that singlet oxygen ( 1 O 2 ) was generated through energy‐transfer pathway.

Language: Английский

Citations

Photocatalyzed chemodivergent aerobic oxidation of naturally occurring Viridicatin and derivatives DOI

Yingxian Li, Hui Wang,

Xuemin Jia

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: June 1, 2024

A chemodivergent reaction is an appealing way to construct molecules with enriched structure diversity in a controlled manner. plethora of methodologies were developed based on this concept, and transition metal-catalysis plays central role among others catalysis systems own its longstanding history. While organo-catalysis, especially photocatalysis, rather limited as these concepts only prevalent the last two decades. With ever-increasing importance such activation pathway would be meaningful direction. Herein, efficient strategy for visible light photocatalysis developed. By employing commercially available Rose Bengal photocatalyst, naturally occurring Viridicatin derivatives can transformed into three different types products through switchable single electron transfer (SET) or energy (EnT) processes. Mechanistic studies have revealed that oxygen reactive center, than carbon, favored, which accounts first example C-O homo-dimerization product.

Language: Английский

Citations