Visible Light-Promoted Ir(III)-Catalyzed Stereoselective Synthesis of Azauracil-C-Nucleosides from 1-Bromosugar DOI

Ramanand Das,

Norein Sakander,

Sanchari Kundu

et al.

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

Published: May 20, 2025

A visible light-promoted, mild, and efficient Ir(III)-catalyzed synthesis of C-nucleosides is reported, utilizing 1-bromosugar as the glycosyl radical precursor 6-azauracil nucleobase. The method exhibits high α-selectivity excellent functional group tolerance. Spectroscopic evidence shows that coupling reaction happens via initial reductive quenching Ir(III) catalyst under light. Density theory calculation reveals reason for complete α-selectivity. Finally, biologically active 6-aza pseudouridine analogues were synthesized, making process a valuable platform C-nucleosides.

Language: Английский

Photoinduced Pd-Catalyzed Formal Asymmetric Allylic Substitution of Piperidine Scaffolds DOI

Weidong Lu,

Zhilin Liu,

Zi‐Hao Liao

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 4384 - 4393

Published: Feb. 26, 2025

Language: Английский

Citations

1
Photoinduced Metal‐/Additive‐Free Difluoromethylation of N‐Heteroaromatics† DOI Open Access
Congjun Zhu, Yangyang Shen, Tao Guo

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 16, 2025

Comprehensive Summary Herein, we report a photo‐induced, metal‐/additive‐free protocol for the difluoromethylation of N ‐heteroaromatics with [bis(difluoroacetoxy)iodo]benzene as reagent. The affords difluoromethylated in moderate to good yield (up 91%). transformation is compatible wide range substrates and has tolerance towards various functional groups. Moreover, synthetic value this method further demonstrated by applications gram‐scale synthesis late‐stage functionalization biologically important molecules.

Language: Английский

Citations

0
Harnessing Visible/UV Light for the Activation and/or Functionalization of C−H Bonds: Metal‐ and Photocatalyst‐Free Approach DOI Open Access
Jitender Bariwal, Erik V. Van der Eycken

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: March 12, 2025

Abstract Photosynthesis in plants has inspired photochemical reactions organic chemistry. Synthetic chemists always seek cost‐effective, operationally simple, averting the use of toxic and difficult‐to‐remove metallic catalysts, atom economical, high product purity reactions. In last few decades, light as a catalyst increased exponentially literature exploded with examples, particularly by using expensive metal complexes, photosensitizers like dyes, hypervalent iodine, or inorganic semiconductors. this report, we have selected interesting examples performed without any photosensitizers. These inherent potential reactants to utilize energy initiate chemical Our main emphasis is highlight structural features that can absorb form an electron donor‐acceptor (EDA) complex during reaction reaction. Considering degree variability reactions, utmost care been taken present most accurate conditions. A short introductory section on will act anchor revolve around discussed explain underlying principle mechanism.

Language: Английский

Citations

0
Excited-State Palladium-Catalyzed Radical Allylic Alkylation: Rapid Access to C2-Allyl Carbohydrates DOI
Wang Yao, Jaclyn N. Mauro, Yue Fu

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 5480 - 5489

Published: March 19, 2025

Language: Английский

Citations

0
Silver-catalyzed direct decarboxylative C H functionalization of azauracils with aliphatic carboxylic acids DOI
Jie Zeng, Hong Zhou, Shenghao Wang

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155619 - 155619

Published: April 1, 2025

Language: Английский

Citations

0
Visible Light-Promoted Ir(III)-Catalyzed Stereoselective Synthesis of Azauracil-C-Nucleosides from 1-Bromosugar DOI

Ramanand Das,

Norein Sakander,

Sanchari Kundu

et al.

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

Published: May 20, 2025

A visible light-promoted, mild, and efficient Ir(III)-catalyzed synthesis of C-nucleosides is reported, utilizing 1-bromosugar as the glycosyl radical precursor 6-azauracil nucleobase. The method exhibits high α-selectivity excellent functional group tolerance. Spectroscopic evidence shows that coupling reaction happens via initial reductive quenching Ir(III) catalyst under light. Density theory calculation reveals reason for complete α-selectivity. Finally, biologically active 6-aza pseudouridine analogues were synthesized, making process a valuable platform C-nucleosides.

Language: Английский

Citations

0