Dual Photosensitizer Cycles Working Synergistically in a C(sp)‐C(sp3) Cross‐Coupling Reaction** DOI Creative Commons

Megan Amy Bryden,

Marco Villa, Andrea Fermi

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(10)

Published: Aug. 16, 2023

Abstract To assess the value and reactivity of new photocatalysts (PCs), their performance should be evaluated in one or more established reactions benchmarked against using known PCs. Here, we our recently developed PC, pDTCz‐DPmS , a C(sp)‐C(sp 3 ) cross‐coupling reaction that had been documented literature. Previous findings indicated this could not proceed absence PC; however, under conditions was case. Without moderate product yield obtained, while increased significantly upon addition . UV‐Vis absorption studies Hantzsch ester (HE) additive acting as competitive absorber light from excitation source, quenching confirmed HE quenched by radical precursor, N ‐(acyloxy)phthalimide. Mechanistic investigations two parallel photosensitization pathways were operation; reductive photocatalytic pathway (using sacrificial photoreductant (employing HE). These work synergistically to enhance target product.

Language: Английский

Solar energy storage to chemical: Photocatalytic CO2 reduction over pristine metal-organic frameworks with mechanistic studies DOI
Syed Shoaib Ahmad Shah, Muhammad Altaf Nazir, Karim Khan

et al.

Journal of Energy Storage, Journal Year: 2023, Volume and Issue: 75, P. 109725 - 109725

Published: Nov. 19, 2023

Language: Английский

Citations

43

Challenges and Future Perspectives in Photocatalysis: Conclusions from an Interdisciplinary Workshop DOI Creative Commons
Sebastian B. Beil, Sylvestre Bonnet, Carla Casadevall

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(8), P. 2746 - 2766

Published: Aug. 8, 2024

Photocatalysis is a versatile and rapidly developing field with applications spanning artificial photosynthesis, photo-biocatalysis, photoredox catalysis in solution or supramolecular structures, utilization of abundant metals organocatalysts, sustainable synthesis, plastic degradation. In this Perspective, we summarize conclusions from an interdisciplinary workshop young principal investigators held at the Lorentz Center Leiden March 2023. We explore how diverse fields within photocatalysis can benefit one another. delve into intricate interplay between these subdisciplines, by highlighting unique challenges opportunities presented each multidisciplinary approach drive innovation lead to solutions for future. Advanced collaboration knowledge exchange across domains further enhance potential photocatalysis. Artificial photosynthesis has become promising technology solar fuel generation, instance, via water splitting CO

Language: Английский

Citations

17

Efficient palladium-catalyzed electrocarboxylation enables late-stage carbon isotope labelling DOI Creative Commons
Gabriel M. F. Batista, Ruth Ebenbauer, Craig S. Day

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: March 22, 2024

Abstract Carbon isotope labelling of bioactive molecules is essential for accessing the pharmacokinetic and pharmacodynamic properties new drug entities. Aryl carboxylic acids represent an important class structural motifs ubiquitous in pharmaceutically active are ideal targets installation a radioactive tag employing isotopically labelled CO 2 . However, direct incorporation via reported catalytic reductive carboxylation (CRC) aryl electrophiles relies on excess , which incompatible with carbon-14 incorporation. Furthermore, application some CRC reactions late-stage limited because low tolerance molecular complexity by catalysts. Herein, we report development practical affordable Pd-catalysed electrocarboxylation setup. This approach enables use near-stoichiometric 14 generated from primary source Ba 3 facilitating single-step pharmaceuticals representative precursors. The proposed isotope-labelling protocol holds significant promise immediate impact programmes.

Language: Английский

Citations

10

Photochemical Reductive Carboxylation of N-Benzoyl Imines with Oxalate Accelerated by Formation of EDA Complexes DOI
Wenwen Liu, Pei Xu,

Hui-Xian Jiang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(13), P. 10053 - 10059

Published: June 20, 2024

Language: Английский

Citations

10

Transition Metal and Photocatalyst Free Arylation via Photoexcitable Electron Donor Acceptor Complexes:Mediation and Catalysis DOI
Alexey A. Volkov, Dmitry I. Bugaenko, Alexander V. Karchava

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(11)

Published: Jan. 15, 2024

Abstract Visible‐light‐activated organic reactions unlock novel avenues for complex molecular transformations, impossible under standard “thermal” conditions, which makes them powerful tools in the arsenal of synthetic chemistry. However, transition metal‐based or photoredox catalysts are often used to ensure productive absorption visible light, might be not desirable medicinal chemistry and industry due toxicity, low sustainability, high cost most photocatalysts. A more environmentally economically benign approach is based on formation transient electron donor‐acceptor (EDA) complexes between two reagents a reagent an additive, that readily absorb acting as internal photosensitizers. Within EDA complex‐based arylation strategies, chemical transformations mediated by noncovalent interaction molecules, namely electron‐poor aryl halides their equivalents electron‐rich nucleophilic additives. Moreover, besides stoichiometric organocatalysis can achieved certain cases through regeneration donor molecules course reaction. Photoexcitation induces single transfer (SET) process generate radical species step. This Review will focus state‐of‐the‐art strategies utilizing halides, aryldiazonium, diaryliodonium, arylsulfonium arylphosphonium salts reactants, published mainly last five years.

Language: Английский

Citations

6

Bidirectional Elongation Strategy Using Ambiphilic Radical Linchpin for Modular Access to 1,4-Dicarbonyls via Sequential Photocatalysis DOI
Akira Matsumoto, Natsumi Maeda, Keiji Maruoka

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(37), P. 20344 - 20354

Published: July 25, 2023

Organic molecules that can be connected to multiple substrates by sequential C-C bond formations utilized as linchpins in multicomponent processes. While they are useful for rapidly increasing molecular complexity, most of the reported linchpin coupling methods rely on use organometallic species strong carbon nucleophiles form bonds, which narrows functional group compatibility. Here, we describe a metal-free, radical-mediated approach using formyl-stabilized phosphonium ylide multifunctional under visible-light photoredox conditions. The present method uses ambiphilic character ylide, serves both nucleophilic and an electrophilic carbon-centered radical source. stepwise controllable generation these intermediates allows photocatalysis involving two mechanistically distinct additions, initiated same photocatalyst one pot with high tolerance. methodology enables bidirectional assembly electronically differentiated alkene fragments thus offers rapid modular access 1,4-dicarbonyl compounds versatile synthetic intermediates.

Language: Английский

Citations

13

Photocatalytic deuterocarboxylation of alkynes with oxalate DOI Creative Commons

Pei Xu,

Hao-Qiang Jiang,

Hui Xu

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(32), P. 13041 - 13048

Published: Jan. 1, 2024

Herein, a catalytic photoredox-neutral strategy for alkyne deuterocarboxylation with tetrabutylammonium oxalate as the carbonyl source and D

Language: Английский

Citations

5

Photoredox-Neutral Deoxygenative Carboxylation of Acylated Alcohols with Tetrabutylammonium Oxalate DOI

Chen-Wei Xu,

Si-Yi Yan,

Hui Xu

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(16), P. 11967 - 11973

Published: July 26, 2024

Herein, a photoredox-neutral strategy for carboxylation of acylated alcohols via C(sp3)–O bond activation and cleavage with tetrabutylammonium oxalate (TBAO) as the carbonyl source reductant well promoter is described. Neither pre-established CO2 atmosphere nor external electron donors are required TBAO crucial transformation. Various primary, secondary, tertiary could be smoothly converted to corresponding aryl acetic acids, which core structures diverse pharmaceutical drugs.

Language: Английский

Citations

4

Organic super-reducing photocatalysts generate solvated electrons via two consecutive photon induced processes DOI Creative Commons
Marco Villa, Andrea Fermi, Francesco Calogero

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(36), P. 14739 - 14745

Published: Jan. 1, 2024

The strong photoreducing abilities of the investigated TADF chromophores is result photogeneration solvated electrons in a consecutive two-photon induced mechanism (ConPies).

Language: Английский

Citations

4

Copper(I) Photoredox Catalysts Bearing Tetradentate Phenanthroline-Based Ligands: Understanding the Interplay between Structure and Function DOI
Angus Olding, Lee Cameron, Le Nhan Pham

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3731 - 3740

Published: Feb. 17, 2025

Language: Английский

Citations

0