NHC‐Catalyzed, Microwave‐Assisted and Base‐Dependent Reactions of Substituted Cinnamaldehydes Towards γ‐Lactones or Saturated Esters DOI Creative Commons
Victoria Magrioti, Evanthia Papadaki,

Antonia Kapoti

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 6, 2024

Abstract N‐Heterocyclic carbenes (NHCs) generated from imidazolium, imidazopyridinium and imidazoquinolinium hydrochlorides in situ using base microwave irradiation were employed as organocatalysts to yield homoenolates cinnamaldehyde its aryl‐substituted analogs. Depending on the catalytic either γ‐lactones prepared when strong tBuOK was used or corresponding saturated ethyl 3‐aryl propionates synthesized with milder DIPEA base. Novel compared commercially available NHCs IMes IDip for their activity. The optimum reaction conditions established broad scope of both reactions investigated 4 most efficient NHCs.

Language: Английский

Divergent functionalization of alkenes enabled by photoredox activation of CDFA and α-halo carboxylic acids DOI Creative Commons
Rahul Giri, Egor S. Zhilin, Dmitry Katayev

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(27), P. 10659 - 10667

Published: Jan. 1, 2024

The direct activation of α-halo carboxylic acids using visible-light-mediated photoredox catalysis facilitates the formation bifunctional radical intermediates, allowing reactivity toward olefins to be fine-tuned by varying solvent system.

Language: Английский

Citations

5

The Diverse Applications of Sodium l-Ascorbate as a Reducing Agent in Organic Synthesis DOI Creative Commons
Letícia Ribeiro Magalhães, Euzébio Guimarães Barbosa, Alessandro K. Jordão

et al.

SynOpen, Journal Year: 2025, Volume and Issue: 09(01), P. 105 - 130

Published: March 1, 2025

Abstract Sodium l-ascorbate is an inexpensive and non-hazardous organic salt derived from ascorbic acid that widely applied as a reducing agent in diverse industrial processes occurs naturally some plants animals. In synthesis it can participate variety of reactions, playing different roles secondary or main reactant to promote wide range chemical transformations, being most commonly used along with metallic catalysts. This graphical review highlights the numerous applications sodium ascorbate reactions.

Language: Английский

Citations

0

Benzophenothiazine/Boronic Acid Cooperative Photocatalysis Enables the Synthesis of γ-Lactones via the [3 + 2] Cycloaddition of α,β-Unsaturated Carboxylic Acids with Olefins DOI

Taichi Yumura,

Takeshi Nanjo, Yoshiji Takemoto

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 4975 - 4983

Published: March 10, 2025

Language: Английский

Citations

0

Application of Lead-Free Metal Halide Perovskite Heterojunctions for the Carbohalogenation of C–C Multiple Bonds DOI Creative Commons
Camilla Callegari,

Costanza Tedesco,

Alessia Corbo

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

A graphitic carbon nitride/lead-free double perovskite heterojunction (g-C3N4/Cs2AgBiCl6) has been adopted as a heterogeneous photocatalyst under visible light irradiation. The employed material enabled the atom transfer radical addition-type carbohalogenation of multiple C-C bonds, including (internal) alkenes and alkynes, with alkyl halides. protocol showed remarkable functional group tolerance, compatible late-stage functionalization natural pharmaceutical derivatives, could be easily scaled up, delivering >1 g desired products.

Language: Английский

Citations

0

Phenothiazine Sulfoxides as Active Photocatalysts for the Synthesis of γ-Lactones DOI Creative Commons
Niklas Hölter,

Nils Rendel,

Leander Spierling

et al.

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

Published: April 2, 2025

N-substituted phenothiazines are prominent and highly effective organic photoredox catalysts, particularly known for their strong reducing capabilities. Despite wide utility, the closely related phenothiazine sulfoxides, which easily form upon oxidation, have been largely overlooked not explored in context of photocatalysis. Herein, we describe discovery application N-phenylphenothiazine sulfoxide as a photocatalyst reductive activation cyclic malonyl peroxides, giving access to complex γ-lactones starting from simple olefins. Detailed mechanistic studies were carried out better understand situ formation active catalyst species commercial precursor, well interconversion photocatalytic mechanism γ-lactone products. Specifically, employed broad range tools, including time-resolved spectroscopy, spectroelectrochemistry, transient UV-vis absorption voltammetry, isotopic labeling, radical trapping experiments, NMR density functional theory (DFT) calculations. The synthetic utility this protocol is demonstrated substrate scope study, highlighting facile spirocyclic γ-lactones, widely recognized biological importance.

Language: Английский

Citations

0

Aerobic oxidative bromination and iodination enabled by alloxan and ascorbic acid to mimic flavin-dependent halogenases DOI Creative Commons
Shiqi Zhang, Guangxun Li, Dongmei Fang

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: April 17, 2025

Language: Английский

Citations

0

Photochemical Michael Addition of Indoles to α,β‐Unsaturated Ketones utilizing Arylazo Sulfones as the Photoacid Generators DOI Creative Commons

Eirini M. Galathri,

Lorenzo Di Terlizzi, Maurizio Fagnoni

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: May 20, 2024

Abstract The Michael‐type addition of indoles represents one the most important C−C bonds forming reactions at their C‐3 position. Herein, we present a mild, versatile and sustainable protocol for efficient preparation β ‐indolylketones via Michael between chalcones or α , ‐unsaturated ketones in presence substituted arylazo sulfones as photoacid generators (PAGs).

Language: Английский

Citations

2

Low‐Impact Synthesis of γ‐Lactones through Photoinduced Baeyer‐Villiger Oxidation of Cyclic Ketones DOI Creative Commons
Maria Chiara Cabua, Viktoria Velichko, Luca Pilia

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(21)

Published: April 5, 2024

Abstract A photocatalyzed oxidation of functionalized cyclobutanones to access γ‐lactones has been performed in acetonitrile at room temperature, using anthraquinone derivatives as catalysts the presence TFA. The best reaction results were obtained by 3 mol % 9,10‐anthraquinone a catalyst under 370 nm irradiation an O 2 environment. scope and limitations this have investigated both 2‐ 3‐substituted cyclobutanones, well enantiopure ketones, obtain full preservation their stereochemical identity after oxidation. process furnishes most cases desired compounds with high purity removal simple filtration, reducing production solvents waste.

Language: Английский

Citations

1

Stereoselective synthesis of naturally-occurring γ-lactones through photoredox catalysis DOI Creative Commons

Derek Mota-Hernández,

Luis Antonio Vázquez-López,

Jorge Victoria-Miguel

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 167, P. 134270 - 134270

Published: Sept. 13, 2024

Language: Английский

Citations

1

Exploring the Reactivity of Melanins as Photocatalysts for Reductive Dehalogenations DOI Creative Commons
Andrea Capucciati,

Valentina Foli,

Pasquale Lioniello

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(20)

Published: March 25, 2024

Abstract Four melanin polymers prepared from different precursors (5,6‐dihydroxyindole, 5,6‐dihydroxyindole 2‐carboxylic acid, 1,8‐dihydroxynaphthalene and dopamine) have been adopted as photocatalysts in the reductive dehalogenation of a series model α‐halogen carbonyl derivatives. The best performing was that obtained which allowed to dehalogenate efficiently both bromomalonate esters phenacyl bromide; on other hand, chloromalonate were almost unreactive under same reaction conditions. Electrochemical control experiments enabled elucidate mechanism, demonstrating key role electrons charge carriers observed photocatalytic process.

Language: Английский

Citations

0