Organometallic Photocatalyst‐Promoted Synthesis and Modification of Carbohydrates under Photoirradiation DOI Open Access
Jing Wang,

Fan Zhou,

Yu‐Ping Xu

et al.

The Chemical Record, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 27, 2024

Carbohydrates are natural, renewable, chemical compounds that play crucial roles in biological systems. Thus, efficient and stereoselective glycosylation is an urgent task for the preparation of pure structurally well-defined carbohydrates. Photoredox catalysis has emerged as a powerful tool carbohydrate chemistry, providing alternative addressing some challenges glycochemistry. Over last few decades, Ir- Ru-based organometallic photocatalysts have attracted significant interest because their high stability, high-energy triplet state, strong visible-light absorption, long luminescence lifetime, amenability to ligand modification. This review highlights recent progress photocatalyst-promoted synthesis modification carbohydrates under photoirradiation, well related benefits drawbacks.

Language: Английский

Photocatalytic cyclization of 3-(2-isocyanophenyl)quinazolin-4(3H)-ones for the construction of quinoxalino[2,1-b]quinazolinones DOI

Xian Wu,

Ling-Li Liu,

Chengli Xiang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(18), P. 2556 - 2559

Published: Jan. 1, 2024

3-(2-Isocyanophenyl)quinazolin-4(3 H )-ones were designed and synthesized as new building units for the construction of novel quinoxalino[2,1- b ]quinazolinones under mild, photocatalytic metal-free conditions.

Language: Английский

Citations

5
C–OH Bond Activation for Stereoselective Radical C-Glycosylation of Native Saccharides DOI
Hao Xie, Sheng Wang, Xing‐Zhong Shu

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(47), P. 32269 - 32275

Published: Nov. 15, 2024

Radical C-glycosylation presents a flexible and efficient method for synthesizing C-glycosides. Existing methods always require multistep processes generating anomeric radicals. In this study, we introduce streamlined approach to produce radicals through direct C-OH bond homolysis of unmodified saccharides, eliminating the need protection, deprotection, or activation steps. These selectively couple with activated alkenes, yielding products high stereoselectivity (>20:1). This is applicable variety native monosaccharides, such as l-arabinose, d-arabinose, d-xylose, l-xylose, d-galactose, β-d-glucose, α-d-glucose, l-ribose, well oligosaccharides including α-lactose, d-(+)-melibiose, acarbose. We also extend amino acid peptide derivatives, demonstrate synthesis an anti-inflammatory agent.

Language: Английский

Citations

4
Photoredox-Catalyzed C-Indolyl/Quinolyl Glycosylation from 2-Styrylisocyanides and Glycosyl Bromides DOI

Yi Jiao,

Xiaoran Shi,

Yiqiang Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(38), P. 8149 - 8153

Published: Sept. 16, 2024

Indole and quinoline structures are present in numerous biologically active molecules, making the synthesis of their glycosylation products a subject extensive research interest drug development. Here, we report photoredox strategy for

Language: Английский

Citations

3
Photoredox-Mediated Radical Addition/Cyclization To Construct Benzannulated 6,5-Spiroketal Glycosides DOI
Chen Li, Shouyun Yu

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

Published: Jan. 30, 2025

We herein present a green and mild photoredox strategy for constructing framework of benzannulated 6,5-spiroketal glycosides. This method employs various O-arylacetylene glycosides aryl ketone acids as the starting materials, facilitating rapid straightforward synthesis with up to 92% yields under catalytic conditions. efficient approach has potential significantly enhance molecular library carbohydrate-based pharmaceuticals.

Language: Английский

Citations

0
A brief account of the application of glycosyl halide as glycosyl radical precursor towards glycosylation through visible light catalysis DOI

Ramanand Das,

Rahul Haldar,

Irshad Ahmad Zargar

et al.

Carbohydrate Research, Journal Year: 2025, Volume and Issue: 554, P. 109537 - 109537

Published: May 17, 2025

Language: Английский

Citations

0
A mild and practical approach to N-CF3 secondary amines via oxidative fluorination of isocyanides DOI Creative Commons
Junliang Fu,

Jun‐Yunzi Wu,

Jiandong Shi

et al.

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

Published: May 26, 2025

N-trifluoromethyl compounds, featuring a CF3 group directly attached to nitrogen, are valuable in medicinal chemistry. Despite substantial advances their synthesis over the past decade, efficient preparation of inherently unstable N-CF3 secondary amines remains challenge synthetic Herein, we present mild and practical method for synthesizing these compounds via oxidative fluorination isocyanides using iodine as oxidant, silver fluoride fluorinating reagent, tert-butyldimethylsilane proton precursor. This approach benefits from simple workup, all reagents by-products can be easily removed through filtration evaporation. protocol features broad substrate scope, good functional tolerance, excellent yields. Additionally, resulting products readily converted into carbamoyl fluorides, building blocks diverse carbonyl derivatives.

Language: Английский

Citations

0
A Radical Activation Strategy for Versatile and Stereoselective N‐Glycosylation DOI

Wenyan Ding,

Xinyu Chen,

Zuyao Sun

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(36)

Published: June 5, 2024

Previous N-glycosylation approaches have predominately involved acidic conditions, facing challenges of low stereoselectivity and limited scope. Herein, we introduce a radical activation strategy that enables versatile stereoselective using readily accessible glycosyl sulfinate donors under basic conditions exhibits exceptional tolerance towards various N-aglycones containing alkyl, aryl, heteroaryl nucleobase functionalities. Preliminary mechanistic studies indicate pivotal role iodide, which orchestrates the formation from subsequent generation key intermediate, configurationally well-defined is subsequently attacked by an N-aglycone in stereospecific S

Language: Английский

Citations

3
Preparing glycosyl benzothiazoles from 2-isocyanoaryl thioethers and glycosyl radicals under thermal conditions DOI

Daqi Liu,

Yang Zhang, Dawen Niu

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(42), P. 5498 - 5501

Published: Jan. 1, 2024

Glycosyl radicals generated from readily available and bench-stable allyl glycosyl sulfones, promoting radical cascade cyclization for preparing benzothiazoles.

Language: Английский

Citations

1
A Radical Activation Strategy for Versatile and Stereoselective N‐Glycosylation DOI

Wenyan Ding,

Xinyu Chen,

Zuyao Sun

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(36)

Published: June 5, 2024

Abstract Previous N‐glycosylation approaches have predominately involved acidic conditions, facing challenges of low stereoselectivity and limited scope. Herein, we introduce a radical activation strategy that enables versatile stereoselective using readily accessible glycosyl sulfinate donors under basic conditions exhibits exceptional tolerance towards various N‐aglycones containing alkyl, aryl, heteroaryl nucleobase functionalities. Preliminary mechanistic studies indicate pivotal role iodide, which orchestrates the formation from subsequent generation key intermediate, configurationally well‐defined is subsequently attacked by an N‐aglycone in stereospecific S N 2 manner to give desired N‐glycosides. An alternative route involving coupling nitrogen‐centered also proposed, affording exclusive 1,2‐ trans product. This novel approach promises broaden synthetic landscape N‐glycosides, offering powerful tool for construction complex glycosidic structures mild conditions.

Language: Английский

Citations

1
Stereoselective Synthesis of C-Aryl-α-Glycosides by Reductive C(sp2)–C(sp3) Cross-Coupling Reaction DOI

Noyuri Kudo,

Suzuka Chiba,

Kazuteru Usui

et al.

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

Published: June 25, 2024

Abstract C-Aryl glycosides have attracted considerable interest as biologically active natural products and O-aryl glycoside mimetics in drug discovery. Here, we describe a straightforward synthesis of C-aryl by photoredox/Ni dual-catalyzed reductive cross-coupling between glycosyl bromides aryl bromides. This methodology enables highly α-stereoselective glucosides, galactosides, mannosides.

Language: Английский

Citations

0