Photoinduced Tandem C‐O Bond Reduction / Ketyl Radical Addition Reactions of α‐Keto‐N,O‐Acetals Enabled by Proton‐Coupled Electron Transfer DOI Creative Commons
Paul Seefeldt, L Edelmann,

Adrian Prudlik

et al.

ChemPhotoChem, Journal Year: 2024, Volume and Issue: 8(8)

Published: March 12, 2024

Abstract The C10a‐acetoxylated tetrahydroazepino[1,2‐ a ]indole‐6,11‐diones are class of tricyclic oxindoles that feature an α‐keto‐ N , O ‐acetal substructure, rendering them highly susceptible to SET reduction followed by fragmentation. In protic medium, they undergo PCET‐assisted two‐step including interposed C−O bond cleavage can be initiated photocatalytically as well cathodic reduction, and which generates nucleophilic ketyl radicals. the presence acrylonitrile DIPEA additional reactants, photoinduced reaction unfolds tandem reduction/ketyl radical conjugate addition, furnish C10a‐reduced, C11‐cyanoethyl‐substituted azepino‐[1,2‐ ]indole derivatives with high stereoselectivity.

Language: Английский

Isonitriles as Alkyl Radical Precursors in Visible Light Mediated Hydro‐ and Deuterodeamination Reactions** DOI Creative Commons
Irene Quirós, María Martín, Miguel Gomez‐Mendoza

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(7)

Published: Dec. 27, 2023

Herein, we report the use of isonitriles as alkyl radical precursors in light-mediated hydro- and deuterodeamination reactions. The reaction is scalable, shows broad functional group compatibility potential to be used late-stage functionalization. Importantly, method general for C

Language: Английский

Citations

18

Recyclable photocatalyst perovskite as a single-electron redox mediator for visible-light-driven photocatalysis gram-scale synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones in air atmosphere DOI Creative Commons
Farzaneh Mohamadpour

Scientific Reports, Journal Year: 2023, Volume and Issue: 13(1)

Published: June 24, 2023

Based on the Biginelli reaction of β-ketoesters, arylaldehydes, and urea/thiourea, we created a green radical synthesis procedure for 3,4-dihydropyrimidin-2-(1H)-ones/thiones. A single-electron redox mediator was applied to solution ethanol in an air environment, at room temperature, with blue LEDs as renewable energy source order create. The objective this research is create halide perovskite that widely available, affordable, recyclable, economically feasible. factor mentioned discussion tolerates variety donating withdrawing functional groups while still offering very fast rate excellent yields. range yields quite uniform (86-94%, average: 90.4%), times quick (4-8 min, 5.8 min). Furthermore, gram-scale cyclization shows it applicable use industry. Additionally, CsPbBr3 stable can be used six row without experiencing significant structural changes or activity loss, which has been extremely helpful meeting industrial needs environmental issues.

Language: Английский

Citations

12

Proflavine (PFH+): as a photosensitizer (PS) biocatalyst for the visible-light-induced synthesis of pyrano [2,3-d] pyrimidine scaffolds DOI Creative Commons
Farzaneh Mohamadpour, Ali Mohammad Amani

Frontiers in Chemistry, Journal Year: 2024, Volume and Issue: 12

Published: March 26, 2024

A sustainable methodology for the synthesis of pyrano [2,3- d ] pyrimidine scaffolds have been developed, employing Knoevenagel-Michael tandem cyclocondensation reaction barbituric acid/1,3-dimethylbarbituric acid, malononitrile, and aryl aldehydes. This study elucidates advancement a environmentally conscious approach to synthesizing this category chemical compounds. In present investigation, novel photosensitizer comprising proflavine (PFH + ) bio-photocatalyst was employed in an aqueous medium, subjected air atmosphere at room temperature, stimulated by blue-light-emitting diode (LED) harness renewable energy. The fundamental objective initiative is utilize (PS) biocatalyst that has recently can be conveniently acquired, priced affordably. photocatalyst, demonstrates ability initiate photoinduced-electron transfer (PET) through exposure visible light. property endows photocatalyst with practical efficient method achieving high effectiveness, energy efficiency, friendly outcomes. current research endeavor examining turnover number (TON) frequency (TOF) pertaining scaffolds. Moreover, it validated cyclization gram-scale feasible various industrial settings.

Language: Английский

Citations

4

Ultrasonic-promoted synthesis of amino methylene bisphosphonates by sulfated choline ionic liquid DOI
G. Manjula,

Reddi Mohan Naidu Kalla,

Araveeti Eswar Reddy

et al.

Research on Chemical Intermediates, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 3, 2025

Language: Английский

Citations

0

Unveiling a carbazole-based photocatalyst for visible-light-driven synthesis of indolyl diarylmethanes and 2-benzimidazoles DOI
Sunil Kumar, K. R. Justin Thomas

Catalysis Science & Technology, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A carbazole-based photocatalyst (MD) incorporating a dicyanovinyl acceptor and exhibiting superior redox potential has been demonstrated for sustainable photocatalytic approach to synthesize indolyl diarylmethanes 2-substituted benzimidazoles.

Language: Английский

Citations

0

Synthesis of a sulfone-modified derivative of boron-sulphur co-doped graphitic carbon nitride photocatalyst for 1,4 NADH regeneration and synthesis of Biginelli end products DOI
Ankit Yadav, Rajesh Kumar Yadav, Kanchan Sharma

et al.

Materials Science and Engineering B, Journal Year: 2025, Volume and Issue: 318, P. 118296 - 118296

Published: April 11, 2025

Language: Английский

Citations

0

Recent Advancement of 1,2,3,5‐Tetrakis(Carbazol‐9‐yl)‐4,6‐Dicyanobenzene (4‐CzIPN) in Photocatalyzed Synthesis of Heterocyclic Compounds DOI

Km Garima,

Vishal Srivastava, Praveen P. Singh

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(17)

Published: May 1, 2025

Abstract 4‐CzIPN is a traditional electron donor and acceptor fluorophore that uses carbazolyl as an donating dicyanobenzene withdrawing source. Its broad redox potential, high chemical resistance wide applicability makes it unique metal‐free photocatalyst. This study summarizes the recent development of photoredox catalyst for variety heterocyclic construction over last four years (2021‐2024).

Language: Английский

Citations

0

Halogenated dicyanobenzene-based photosensitizer (3DPAFIPN) as a thermally activated delayed fluorescence (TADF) used in gram-scale photosynthesis 3,4-dihydropyrimidin-2-(1H)-one/thione derivatives via a consecutive visible-light-induced electron-transfer pathway DOI Creative Commons
Farzaneh Mohamadpour, Ali Mohammad Amani

Frontiers in Chemistry, Journal Year: 2024, Volume and Issue: 12

Published: March 1, 2024

Background: Organic dyes often have shorter lifetimes in the excited state, which is a major obstacle to development of effective photoredox methods. The scientific community has shown great deal interest certain class organic chromophores because their unique characteristics and effectiveness. One characteristic molecules under research thermally activated delayed fluorescence (TADF), only observed with tiny energy gap (often less than 0.2 eV) between lowest two states, i.e., singlet state (S 1 ) triplet (T ). extended states arising from TADF simplicity redox potentials may be altered make isophthalonitrile family an attractive option for photocatalyst applications. Methods: Biginelli reaction β -ketoesters, arylaldehydes, urea/thiourea been used build sustainable technique production 3,4-dihydropyrimidin-2-(1 H )-one/thione derivatives. In present study, green radical synthesis approach this compounds addressed depth. As photocatalyst, new halogenated dicyanobenzene-based photosensitizer was employed study. renewable source by blue LED, it dissolved ethanol, at room temperature air atmosphere. primary objective employ novel donor-acceptor (D-A) based on cyanoarene that affordable, easily available, innovative. Findings: 3DPAFIPN [2,4,6-tris(diphenylamino)-5-fluoroisophthalonitrile] induces single-electron transfer (SET) response visible light, offering straightforward, eco-friendly, highly efficient process. Additionally, we determined derivatives turnover frequency (TOF) number (TON). It also demonstrated gram-scale cyclization workable method industrial purposes.

Language: Английский

Citations

3

Rose bengal photocatalyzed expeditious multicomponent synthesis of 3,4‐dihydropyrimidin‐2‐(1H)‐ones/thiones under visible light irradiation DOI

Divyani P. Patel,

Vishwa K. Patel,

Satish K. Singh

et al.

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: 61(9), P. 1455 - 1461

Published: July 10, 2024

Abstract The combination of visible light, a renewable and green energy source, rose bengal, non‐toxic organic dye as photoredox catalyst, is an easy efficient method for synthesizing 3,4‐dihydropyrimidin‐2(1 H )‐ones/thiones in EtOH at ambient temperature very short reaction time. present work offers simple operation, workup, rapid conversion, excellent product yields, while accommodating wide range substrates. Rose bengal‐based photocatalytic approach permits foremost sustainability, which delivers economic environmental rewards.

Language: Английский

Citations

3

A new role for concentrated solar radiation (CSR) as a renewable heat source for the catalyst-solvent free synthesis of tetrahydrobenzo[b]pyran scaffolds DOI Creative Commons
Farzaneh Mohamadpour

Scientific Reports, Journal Year: 2023, Volume and Issue: 13(1)

Published: July 17, 2023

Abstract Increased energy consumption as a result of population growth and industrialization necessitates the use renewable sources in field chemistry. Nonrenewable release not only greenhouse gases but also other hazardous pollutants that are damaging to all living things. This plainly mandates researchers' source is both environmentally friendly cost-effective. study shows (sunlight) can be used synthesize tetrahydrobenzo[ b ]pyran scaffolds using Knoevenagel–Michael cyclocondensation aldehyde derivatives, malononitrile, dimedone via three-condensation domino reaction. research establishes new role for solar synthesis under catalyst-solvent-free conditions, with outstanding yields, shorter reaction time, great atom economy. cyclization may done on gram scale free, safe, clean from concentrated radiation (CSR), indicating reaction's potential industrial applications.

Language: Английский

Citations

8