Cited by Photocatalytic multi-component synthesis of ester-containing quinoxalin-2(1H)-ones using water as the hydrogen donor

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors DOI

Ziyan Zhang, Vladimir Gevorgyan

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(11), P. 7214 - 7261

Published: May 16, 2024

In recent years, visible light-induced reactions of diazo compounds have attracted increasing attention in organic synthesis, leading to improvement existing reactions, as well the discovery unprecedented transformations. Thus, photochemical or photocatalytic generation both carbenes and radicals provide milder tools toward these key intermediates for many valuable However, vast majority transformations represent new reactivity modes compounds, which are achieved by decomposition photoredox catalysis. particular, use a redox-active photocatalysts opens avenue plethora radical reactions. The application methods led inaccessible classical associated with metal carbenes. most cases, act sources but can also serve acceptors. Importantly, described processes operate under mild, practical conditions. This Review describes this subfield compound chemistry, particularly focusing on advancements.

Language: Английский

Citations

Photocatalytic Synthesis of Indanone, Pyrone, and Pyridinone Derivatives with Diazo Compounds as Radical Precursors DOI

Yang Xie,

Ye‐Peng Bao,

Xiao-Yan Zhuo

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1393 - 1398

Published: Feb. 12, 2024

We disclose herein a photocatalytic radical cascade cyclization of diazoalkanes for the divergent synthesis important carbocycles and heterocycles. Under optimal reaction conditions, various indanone, pyrone, pyridinone derivatives can be obtained in moderate to good yields. Mechanistic experiments support formation carbon-centered radicals from through proton-coupled electron transfer process. Scale-up using continuous flow technology useful downstream application formed heterocycles further render strategy attractive valuable.

Language: Английский

Citations

Semiheterogeneous Photoredox Catalysis: Synthesis of 3-Sulfonylquinolines via Radical Multicomponent Cascade Annulation DOI

Xiao Li, Jun Jiang, Xiang Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13782 - 13788

Published: Sept. 2, 2024

An efficient photocatalytic protocol combining heterogeneous semiconductors as photocatalysts and NHPI a redox reagent was disclosed. Under this protocol, 3-sulfonylquinolines were formed in up to 92% yield via multicomponent radical cascade annulation. Good substituent tolerance gram-scale reaction showed the potential fine chemicals modification pharmaceutical synthesis.

Language: Английский

Citations

General Synthesis of N-Alkylindoles from N,N-Dialkylanilines via [4 + 1] Annulative Double C–H Functionalization DOI

Bowen Zhang, Frederik R. Erb, Aristidis Vasilopoulos

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(49), P. 26540 - 26544

Published: Nov. 29, 2023

Strategies enabling the construction of indoles and novel polycyclic heterocycles from simple building blocks streamline syntheses in synthetic medicinal chemistry. Herein, we report a C–H functionalization approach to N-alkylindoles proceeding via double, site-selective C(sp3)–H/C(sp2)–H [4 + 1] annulation readily accessed N,N-dialkylanilines. This protocol features hydrogen atom transfer by tuned N-tBu amidyl radical addition sulfonyl diazo coupling partner, which promotes highly homolytic aromatic substitution (hetero)aromatic core. Mild decarboxylation product enables overall introduction carbyne equivalent into N,N-dialkylaniline scaffold. Furthermore, site-selectivity mild conditions indolization facilitate direct access N-alkyl indole scaffolds late-stage (LSF) settings.

Language: Английский

Citations

Photocatalytic Synthesis of Isoquinolinediones via the Cascade Reaction of N-Alkyl-N-methylacrylamides with Diazo Compounds DOI

Chenyue Zhao,

Heran Yang, Kai Xu

et al.

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

Published: March 25, 2025

Carbon radicals generated from acceptor diazo compounds prefer to add electron-rich olefins and heteroarenes due their containing electron-withdrawing groups. Herein, a cascade reaction of with electron-deficient is developed. In the presence visible light Ru catalyst, generate carbon via proton-coupled electron transfer process, followed by addition various N-alkyl-N-methylacrylamides subsequent cyclization give series acyl-substituted isoquinolinediones.

Language: Английский

Citations

Photolytic Access to Oxaspirodecanes and Chromenes from Vinyldiazo Ester Cycloaddition with p-Quinones: A Vinylcarbene Is Not Involved DOI

Soumen Biswas,

Ramon Trevino,

Seth O. Fremin

et al.

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

Published: March 26, 2025

Synthetic methods that provide access to skeletally diverse heterocyclic motifs are poised accelerate drug discovery and streamline the synthesis of advanced intermediates materials. However, development such synthetic necessitates leveraging previously unexplored mechanistic pathways. We report herein an efficient blue light-emitting diode light-induced reaction vinyldiazoacetates quinones produces spirocyclic dihydrofurans, featuring synthetically challenging oxaspiro[4,5]decane core numerous medicinal agents, agrochemicals, natural products. In a departure from well-established photochemical reactivity diazo compounds, these reactions do not involve vinylcarbene formed by photolytic dinitrogen extrusion. Instead, they result photoexcitation quinone its triplet state with subsequent energy transfer vinyldiazo ester. The addition vinylogous carbon vinyldiazoacetate oxygen affords diradical collapses dihydrofuran upon loss dinitrogen. A strain release-driven Bro̷nsted acid-catalyzed rearrangement products unravels fused bicyclic ring system equally medicinally valuable chromenes, enabling facile skeletal diversification important motifs.

Language: Английский

Citations

Hybrid Carbon Nitride/Cobalt Phthalocyanine Nanocomposites for Efficient Photocatalytic Hydrogen Generation DOI

Lakshman Sundar Arumugam,

Javier E. Durantini, Jorge Follana‐Berná

et al.

ACS Applied Energy Materials, Journal Year: 2025, Volume and Issue: unknown

Published: April 4, 2025

Language: Английский

Citations

Photocatalytic C−C bond formation and cleavage reactions based on graphitic carbon nitride semiconductor materials DOI

Wenjie Zhang,

Zeyao Liang,

Xiaoquan Yao

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134651 - 134651

Published: April 1, 2025

Language: Английский

Citations

Photocatalyst‐Free Visible Light‐Induced C(sp²)−H Arylation of Quinoxalin‐2(1H)‐ones and Coumarins DOI

Dingzhe Yu,

Wenjing Yang,

Shuicai Chen

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(44)

Published: June 3, 2024

Herein, we describe a visible light-induced C(sp

Language: Английский

Citations

Visible-Light-Promoted C3-Sulfenylindoles with Arylsulfonyl Chlorides via Electron Donor–Acceptor Complex DOI

Ziqian Xue, Wenjing Yang,

Qiuzhan Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7591 - 7597

Published: May 9, 2024

In this study, we present an efficient approach for the synthesis of 3-sulfenyl indoles through electron donor–acceptor (EDA) complex-promoted photoreaction. This sulfenylation reaction leverages sulfonyl chlorides as sulfur source and employs PPh3 reductant without need any transition-metal catalyst or photocatalyst. At same time, relaxation process excited EDA complex was theoretically investigated at method multiconfiguration second-order perturbation//complete active space self-consistent field/PCM level theory, which involves π bond injecting to antibonding orbital S–Cl in arylsulfonyl chlorides.

Language: Английский

Citations