Visible Light‐Induced Imide Alkylation of Azauracils with Aryl Diazoesters DOI

Sudhir Kumar Hota,

Sandip Murarka

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 19(3)

Published: Dec. 6, 2023

A visible light-induced green and sustainable N-H functionalization of (aza)uracils with α-diazo esters leading to imide alkylation is described. The reaction does not require any catalyst or additive proceeds under mild conditions. Moreover, an intriguing three component coupling was observed when were allowed react in cyclic ethers (e. g. 1,4-dioxane, THF) as a solvent. Both the insertion three-component features broad scope good excellent yields appreciable functional group tolerance. Notably, divergent method enables modification natural products pharmaceuticals, thereby facilitates access potentially biologically active compounds.

Language: Английский

A General Electron Donor–Acceptor Photoactivation Platform of Diaryliodonium Reagents: Arylation of Heterocycles DOI

Prahallad Meher,

Satya Prakash Panda,

Sanat Kumar Mahapatra

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(46), P. 8290 - 8295

Published: Nov. 14, 2023

We report a photoredox system comprising sodium iodide, triphenyl phosphine, and N,N,N',N'-tetramethylethylenediamine (TMEDA) that can form self-assembled tetrameric electron donor-acceptor (EDA) complex with diaryliodonium reagents (DAIRs) furnish aryl radicals upon visible light irradiation. This practical mode of activation DAIRs enables arylation an array heterocycles under mild conditions to provide the respective heteroaryl-(hetero)aryl assembly in moderate excellent yields. Detailed mechanistic investigations photophysical DFT studies provided insight into reaction mechanism.

Language: Английский

Citations

29
Organophotoredox-Catalyzed Arylation and Aryl Sulfonylation of Morita–Baylis–Hillman Acetates with Diaryliodonium Reagents DOI

Sudip Senapati,

Sushanta Kumar Parida,

Sayali Sunil Karandikar

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(43), P. 7900 - 7905

Published: Oct. 26, 2023

We report an organophotoredox-catalyzed stereoselective allylic arylation of MBH acetates with a palette diaryliodonium triflates (DAIRs) to provide the corresponding trisubstituted alkenes in moderate good yields. The method could be extended three-component coupling involving 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) as sulfur dioxide surrogate for synthesis biologically relevant sulfones. Both these reactions were carried out under mild conditions featuring broad scope, robustness, and appreciable functional group tolerance.

Language: Английский

Citations

27
Visible Light-Induced Radical Cascade Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF2H-Substituted Polycyclic Imidazoles DOI Creative Commons
S.J. Lin, Yuanyuan Deng,

Hanxun Zhong

et al.

ACS Omega, Journal Year: 2024, Volume and Issue: 9(26), P. 28129 - 28143

Published: June 19, 2024

An efficient and mild protocol for the visible light-induced radical cascade difluoromethylation/cyclization of imidazoles with unactivated alkenes using easily accessible bench-stable difluoromethyltriphenylphosphonium bromide as precursor -CF

Language: Английский

Citations

4
Visible-Light-Mediated Cascade 1,4-Hydrogen Atom Transfer versus Dearomative Spirocyclization of N-Benzylacrylamides: Divergent Access to Functionalized γ-Ketoamides and 2-Azaspiro[4.5]decanes DOI
Chandra Shekhar Nishad, Ashish Kumar, Kamaldeep Kaur

et al.

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

Published: Jan. 14, 2025

Visible-light-driven metal- and photocatalyst-free cascade 1,4-HAT dearomative spirocyclization of N-benzylacrylamides are described for sustainable synthesis a variety pharmaceutically important γ-ketoamides 2-Azaspiro[4.5]decanes in one pot good to excellent yields. Readily accessible nontoxic materials, expensive Ir or Ru mild conditions, functional group tolerance, operational simplicity, scalability enhance the practical value this protocol. Mechanistic studies reveal that acyl radicals generated from α-oxocarboxylic acids trigger rare spirocyclization. The synthetic potential environmentally benign method is further showcased by late-stage functionalization drug molecules, amino acid, peptides.

Language: Английский

Citations

0
Photoinduced Vicinal Difunctionalization of Diaryliodonium Salts To Access Bis(tetraphenylphosphonium) Salts DOI
Yu Wang, Limin Wang, Jianwei Han

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(4), P. 1012 - 1017

Published: Jan. 21, 2025

Vicinal bis(tetraarylphosphonium) salts have scarcely been reported in the literature. In this study, we demonstrate that visible-light-induced difunctionalization of ortho-trifluoromethylsulfonylated diaryliodonium conveniently furnishes bis(phosphonium) without additional catalysts or photoinitiators. The methodology establishes a practical platform for preparation using readily available tertiary phosphines. are anticipated to garner great deal interest catalytic and medicinal chemistry.

Language: Английский

Citations

0
Photo-induced decarboxylative radical cascade cyclization of unactivated alkenes: access to CF- and CF2-substituted ring-fused imidazoles DOI Creative Commons
Hui-Nan Wang, Shaohui Lin, Hui Hong

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(16), P. 12739 - 12745

Published: Jan. 1, 2025

A mild and effective visible-light-induced decarboxylative radical cascade reaction of olefin-containing imidazoles α-fluorinated carboxylic acids, has been developed to afford monofluoromethylated or aryldifluoromethylated polycyclic imidazoles.

Language: Английский

Citations

0
Electrochemical oxidative monofluoromethylation of N-acryl-2-aryl benzimidazoles: access to CFH 2 -containing benzimidazo[2,1-a]isoquinolin-6(5H)-one derivatives DOI

Guojie Yin,

C. ZHANG,

Qiong Liu

et al.

Synthetic Communications, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 11

Published: April 21, 2025

Language: Английский

Citations

0
Recent advances in the synthesis of benzimidazolo[2,1-a]isoquinoline-6(5H)-one derivatives from N-methylacryloyl-2-arylbenzimidazoles DOI

Qinggang Mei,

Qinghan Li

Tetrahedron, Journal Year: 2024, Volume and Issue: 160, P. 134050 - 134050

Published: May 25, 2024

Language: Английский

Citations

3
Photoinduced decarboxylative radical cascade alkylation/cyclization of benzimidazole derivatives with aliphatic carboxylic acid via ligand-to-iron charge transfer DOI

Yan Xu,

C. Wang,

Chun Lv

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(33), P. 14684 - 14689

Published: Jan. 1, 2024

The photoinduced decarboxylative radical cascade alkylation/cyclization method with various benzimidazole moieties bearing unactivated alkenes efficiently synthesizes polycyclic benzimidazoles via LMCT processes.

Language: Английский

Citations

3
Copper-catalyzed tandem cyclization/arylation of α,β-alkynic hydrazones with diaryliodonium salts: synthesis of N-arylpyrazoles DOI

Sushanta Kumar Parida,

Saurav Joshi,

Sandip Murarka

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(28), P. 5784 - 5789

Published: Jan. 1, 2023

A copper-catalyzed efficient method for the synthesis of a diverse variety substituted N-aryl pyrazoles from readily available α,β-alkynic N-tosyl hydrazones and diaryliodonium triflates is realized. This one-pot multi-step methodology features broad scope with good yields, scalability, appreciable functional group tolerance. Detailed control experiments reveal that reaction proceeds through tandem cyclization/deprotection/arylation events where copper catalyst plays distinct role.

Language: Английский

Citations

7