Photoredox Radical Cascade Cyclization of 2‐Alkynylarylnitriles in Visible Light: Direct Access to 3‐Amino‐1‐indenones DOI

Shruti Rajput,

Dikshita Garg,

Nidhi Jain

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(9), P. 2072 - 2078

Published: March 1, 2024

Abstract A photoinduced direct synthesis of 3‐amino‐1‐indenones via radical cascade cyclization strategy is demonstrated. The methodology involves a domino reaction between 2‐alkynylarylnitrile and N ‐aminopyridinium salt captures the reactivity in‐situ generated nitrogen‐centered (NCR) in visible light. Multiple bond‐forming events including C−N, C−C, C−O take place sequentially on enabling construction 3‐amino‐1‐indenone core at room temperature 35–76% yield. preliminary biological screening synthesized compounds indicative their potent anti‐cancer property.

Language: Английский

General Electron-Donor-Acceptor Complex Mediated Thioesterification Reaction via Site-Selective C-H Functionalization using Aryl Sulfonium Salts DOI

Roshan I. Patel,

Barakha Saxena,

Anuj Sharma

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(19), P. 10265 - 10274

Published: Jan. 1, 2024

We herein describe a versatile electron–donor–acceptor (EDA) mediated thioesterification reaction using aryl sulfonium salt (acceptor) with potassium thioacid salts (donor) under visible light irradiation.

Language: Английский

Citations

5
Multicomponent reactions to access S-aryl dithiocarbamates via an electron donor–acceptor complex under open-to-air conditions DOI

Yisong Tang,

Yougen Cai,

Zhiwei Xie

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(7), P. 1378 - 1385

Published: Jan. 1, 2024

An efficient transition-metal/photocatalyst-free visible-light-driven one-pot three-component reaction between thianthrenium salts, carbon disulfide and amines under air atmosphere for the preparation of S -aryl dithiocarbamates is developed.

Language: Английский

Citations

4
Synthesis of dioxapropellanes using Mn(III)-based oxidative tandem cyclization of tetracarbonyl compounds with diarylethenes DOI Open Access
Keisuke Shibuya,

Ayaka Chikamatsu,

Kazuki Hisano

et al.

Bulletin of the Chemical Society of Japan, Journal Year: 2024, Volume and Issue: 97(3)

Published: Jan. 29, 2024

Abstract The Mn(III)-based oxidation of tetracarbonyl compounds with 1,1-diarylethenes formed dioxapropellanes. use methylenebis(3-hydroxycyclohex-2-en-1-one)s as a compound led to the production 3,4,5,6,7,9-hexahydro-8H-4a,9a-(epoxyethano)xanthene-1,8(2H)-diones in good yields. Although reaction competed self-cyclization form 3,5,6,7-tetrahydro-4H-spiro[benzofuran-2,1′-cyclohexane]-2′,4,6′-triones, it could be controlled by adding co-solvent formic acid at room temperature. reactions alkyl- and aryl-substituted resulted corresponding dioxapropellanes diastereomixture. formation diastereomers is explained steric hindrance intermediate carbocations during tandem cyclization. using 2-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)butane-1,4-diones 2,2′-methylenebis(3-hydroxycyclopent-2-en-1-one)s also produced structure determination products pathway for are discussed.

Language: Английский

Citations

4
DBU‐Promoted [3 + 2] Cyclization/Retro‐Mannich Cascade Reaction of N‐Aminoisoquinolinium and N‐Aminoquinolinium Derivatives with para‐Quinone Methides DOI
Shaohong Ma, Mingyang Chen, Zifeng Yang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(9), P. 2003 - 2007

Published: March 12, 2024

Abstract A DBU‐promoted [3+2] cyclization/retro‐Mannich cascade reaction of N ‐aminoisoquinolinium and ‐aminoquinolinium derivatives with para ‐quinone methides has been established, employing a C=C double bond cleavage. broad range salts, are well tolerated, providing the corresponding rearrangement products. Moreover, scaled‐up reactions diverse derivatizations products were also investigated discussed.

Language: Английский

Citations

4
Cross-Coupling of Carbonyl Derivatives and N-Arylamines Enabled by Visible Light for Easy Access to 1,2-Amino Alcohols DOI
Xu Yan, Hongcheng Zhuang,

Yulin Song

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(2), P. 1078 - 1084

Published: Jan. 7, 2025

We disclosed a new strategy for the synthesis of 1,2-amino alcohols enabled by visible light without requirement photocatalyst and metal. Under irradiation at 400 nm, reaction carbonyl derivatives N-arylamines proceeds via an electron-donor-acceptor (EDA) intermediate, obtaining diverse vicinal amino decorated with two-electron-rich/-deficient aryl group.

Language: Английский

Citations

0
Catalytic enantioselective synthesis of α-C chiral sulfones enabled by merging photoactive electron donor-acceptor complexes with nickel catalysis DOI Creative Commons

Zemin Lai,

Ying Xie, Lele Huang

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: 16(10), P. 4352 - 4359

Published: Jan. 1, 2025

α-C chiral sulfones are privileged building blocks widely found in pharmaceuticals, agrochemicals, natural products, and ligands. Although many nucleophilic or electrophilic protocols have been developed for their construction, radical-based asymmetric catalysis, especially that involving photoactive electron donor-acceptor (EDA) complexes, remains a significant unmet challenge. Herein, we present the first catalytic production of enabled by merging EDA complex with Ni catalyst. With this cooperative catalysis system, wide range achieved good yields excellent enantioselectivities (53 examples, up to 99% yield, 99 : 1 er). The synthetic utility protocol is further demonstrated synthesis selective MMP-3 (stromelysin-1) inhibitor. Detailed mechanistic spectroscopic studies suggest newly identified type generated from sulfonyl chlorides Hantzsch esters (HEs) crucial success as precursor radicals.

Language: Английский

Citations

0
Visible Light-Mediated Selective Synthesis of β-Amino Sulfide Scaffolds via Dual Role of N-Iodosuccinimide DOI

Jaehee Sim,

K P Sujith,

Anna Lee

et al.

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

Published: March 6, 2025

The synthesis of β-amino sulfides is significant in organic chemistry. However, challenges such as achieving regioselectivity and the limited availability starting materials remain unresolved. In this study, we present a visible light-mediated method for selective sulfide scaffolds. Remarkably, two distinct types were selectively synthesized through dual role N-iodosuccinimide, which functions either reactant or an activator construction target

Language: Английский

Citations

0
Visible-Light-Mediated Synthesis of Anomeric S-Aryl Glycosides via Electron Donor–Acceptor Complex Using Thianthrenium Salts DOI Creative Commons

Zhuoyi Zhou,

Yufeng Zhang, Zhiqiang Yu

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(6), P. 1315 - 1315

Published: March 14, 2025

S-Aryl glycosides are not only popular glycosyl donors in carbohydrate chemistry but also serve as valuable tools various biological studies, which has brought significant attention to their preparation. However, there remains a pressing need for greener synthesis methods this area. In response, mild, sustainable, and metal- photocatalyst-free electron donor–acceptor (EDA)-mediated approach synthesizing using 1-thiosugar aryl thianthrenium salt was developed. Our strategy utilizes the donor, overcoming traditional reliance on electron-rich thiols, such or carbonyl typically required forming EDA complexes.

Language: Английский

Citations

0
Dynamic Self-Assembled Systems of Photoinert N-Propargyl Amides Enable Red-Light Supramolecular Photocatalysis DOI
Sathi Sahoo, Tarun Kumar Dinda, Prasenjit Mal

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

Language: Английский

Citations

0
Visible Light-Induced Alkylation of Malononitrile-Assisted Ketones through Deaminative Couplings DOI

Vadla Shiva Prasad,

Silari Mohana Krishna,

Vadithya Ranga Rao

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 25, 2025

The direct alkylation of carbonyl compounds at α & β positions represents a significant challenge. Here, we report catalyst-free visible light-induced deaminative that efficiently produces α, β-alkylated malononitrile-assisted ketones. Mechanistic studies suggested an EDA complex is formed by the Katritzky salt and carbanion malononitrile-aided ketones, which permits disruption C-N bonds generation alkyl radicals. Remarkably, this strategy eliminates need for metal catalysts, additives, ligands offering enhanced environmental sustainability features mild, catalyst-free, broad functional group tolerance. Our optimized condition under blue LED light yielded regio isomers ketones in good to excellent yields with diverse electronic properties substitutions. Implementation flow setup batch protocol efficiency reaction, demonstrating robustness organic synthesis.

Language: Английский

Citations

0