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

A Cascade C(sp3)−H Annulation Involving C(alkyl),C(alkyl)‐Palladacycle Intermediates DOI Open Access
Liwei Zhou,

Xiahong Chen,

Qiong Peng

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(45)

Published: July 25, 2024

Abstract C−H bond functionalization involving C , ‐palladacycle intermediates provides a unique platform for developing novel reactions. However, the vast majority of studies have been limited to transformations (aryl), ‐palladacycles. In sharp contrast, catalytic reactions (alkyl), (alkyl)‐palladacycles rarely reported. Herein, we disclose an unprecedented cascade C(sp 3 )−H annulation (alkyl)‐palladacycles. this protocol, alkene‐tethered cycloalkenyl bromides undergo intramolecular Heck/C(sp activation generate (alkyl)‐palladacycles, which can be captured by α ‐bromoacrylic acids afford tricyclic fused pyridinediones. addition, strategy also applied indole‐tethered construct pentacyclic pyridinediones via suquential Heck dearomatization/C(sp activation/decarboxylative cyclization. Notably, removal in reaction build interesting skeleton containing four‐membered ring. Preliminary mechanistic experiments indicate that five‐membered serve as key intermediates. Meanwhile, density functional theory (DFT) calculations provided insights into pathway.

Language: Английский

Citations

5

Diversity in glycochemistry through metal-catalyzed reactions DOI Creative Commons
Angélique Ferry

Comptes Rendus Chimie, Journal Year: 2025, Volume and Issue: 28(G1), P. 199 - 213

Published: Feb. 27, 2025

The importance and ubiquity of glycosides in both compounds interest biological processes make these biomolecules an interesting topic study. development unnatural analogues is equally compelling has already led to the production several marketed drugs. discovery novel carbohydrates thus a field interest. In order open up this chemical space, it necessary set new efficient synthetic methods, which lead diverse glycosides, some could become beneficial compounds. This account deals with benefits presented by metal-catalyzed reactions, especially cross-couplings C–H functionalization, enable glycoside diversity. L'importance et l'omniprésence des dans composés d'intérêt les processus biologiques font de ces biomolécules motifs intéressants. Le développement d'analogues non naturels est d'importance déjà permis d'accéder nombreux médicaments. La découverte nouveaux donc un domaine d'intérêt. Afin d'ouvrir l'espace chimique, il nécessaire mettre au point nouvelles méthodes synthèse efficaces permettant à une diversité dont certains pourraient se révéler être chefs file. Cet article rapporte le bénéfice réactions métallo-catalysées, en particulier couplages croisés la fonctionnalisation C–H, pour accéder glycosides.

Citations

0

Regulating transient optical responses in twisted bilayer WS2 DOI

Zhongbei Tian,

Dawei He,

Mohan Huang

et al.

Nanotechnology, Journal Year: 2025, Volume and Issue: 36(18), P. 185202 - 185202

Published: March 28, 2025

Abstract The optical response manipulation of two-dimensional materials is crucial for designing and optimizing high-performance optoelectronic devices. Previously, modulation in semiconductors primarily relied on adjusting carrier density through excitation or charge injection using the energy band-filling effect. Recently, twist angle has been found to tune properties van der Waals structure, but its impact transient remains unexplored. Herein, we demonstrate that can effectively regulate behaviors by tracing evolution responses twisted bilayer WS 2 from 0° 60°. Both Raman PL spectra consistently show bilayers are highly dependent angle. Exciton behavior phonon modes exhibit similarity at angles near 60°, significantly change as approaches 30°. Moreover, was carefully investigated a femtosecond pump-probe technique. results reveal significant decrease thermalization/relaxation time exciton formation/recombination with ∼31.0°, compared ∼2.9° ∼58.9°, which be attributed accumulation intralayer carriers due weakened interlayer coupling. These modulate 2D materials. Our study elucidates dynamic provides new insights future photonic

Language: Английский

Citations

0

Modular Synthesis of Polysubstituted α-Phosphorylated Arenes via the Catellani Strategy DOI
Chen Chen,

Jia-Hui Song,

Luyao Ding

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5770 - 5775

Published: June 28, 2024

In this paper, we described a palladium/norbornene-catalyzed

Language: Английский

Citations

3

Synthesis of 1,2-Disubstituted C-Aryl Glycosides via Palladium/Norbornene Cooperative Catalysis DOI

Penggang Zhao,

Lili Li,

Fang Shi

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4711 - 4715

Published: May 29, 2024

The Catellani reaction offers an opportunity to address multiple chemical bonds in a single pot. However, it is still quite challenge construct fully substituted olefins via this strategy, especially electron-rich, unstable, and highly functionalized glycals. Herein we report the first palladium-catalyzed for direct preparation of 1,2-disubstituted C-aryl glycosides from easily available 2-iodoglycals, bromoaryl, alkene/alkyne substrates. This transformation exhibits wide substrate scope, accommodating diverse functional groups intricate molecular frameworks. innovative reactivity efficient pathway valuable carbohydrate analogues building blocks, facilitating novel strategic bond disconnections broadening landscape palladium catalysis.

Language: Английский

Citations

2

Reactivity Switch in Glycal Dienes toward Different Nucleophiles: Mechanistic Insight and Applications toward the Synthesis of Naphthalene-Fused Pyran Derivatives DOI

Ram Pratap Pandey,

Bindu Tiwari,

Navneet K. Sharma

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11502 - 11512

Published: Aug. 2, 2024

The stereo- and regioselective formation of chiral molecules is an interesting important topic in organic synthesis due to its wide applicability intricacy during synthesis. Herein, we disclose a method for the selective functionalization glycal dienes synthesizing different glycosides branched sugars regioselectively. methodology broad regarding substrate scope which various nucleophiles glycals were explored. Furthermore, delve into converting synthesized products naphthalene-fused pyran derivatives, achieved through 4 + 2 cycloaddition followed by aromatization. Additionally, conducted density functional theory studies gain insight when employed.

Language: Английский

Citations

2

Stereoselective Synthesis of C‐Vinyl Glycosides via Nickel‐Catalyzed Cross‐Electrophile Couplings of 1,2‐Glycosyl Orthoesters and Vinyl Halides DOI
Xin Wang,

Anrong Chen,

Shiyin Zhao

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(23), P. 3029 - 3034

Published: Aug. 21, 2024

Comprehensive Summary A highly stereoselective nickel‐catalyzed cross‐electrophile coupling of readily accessible, novel, stable oxygen‐based glycosyl radical precursors, specifically 1,2‐glycosyl orthoesters, is developed. This approach offers an effective pathway to synthesize diverse C ‐vinyl glycosides, characterized by good yields, excellent stereoselectivity, mild reaction conditions, a broad substrate scope, and versatile transformations the resulting products.

Language: Английский

Citations

2

Synthesis of C-glycosides enabled by palladium-catalyzed glycosylation reactions DOI

Wenli Tong,

Jie‐Ping Wan, Jianchao Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6918 - 6941

Published: Jan. 1, 2024

This review highlights the recent progress in palladium-catalyzed C -glycosylation reactions for synthesis of -glycosides.

Language: Английский

Citations

1

A Cascade C(sp3)−H Annulation Involving C(alkyl),C(alkyl)‐Palladacycle Intermediates DOI
Liwei Zhou,

Xiahong Chen,

Qiong Peng

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(45)

Published: July 25, 2024

Abstract C−H bond functionalization involving C , ‐palladacycle intermediates provides a unique platform for developing novel reactions. However, the vast majority of studies have been limited to transformations (aryl), ‐palladacycles. In sharp contrast, catalytic reactions (alkyl), (alkyl)‐palladacycles rarely reported. Herein, we disclose an unprecedented cascade C(sp 3 )−H annulation (alkyl)‐palladacycles. this protocol, alkene‐tethered cycloalkenyl bromides undergo intramolecular Heck/C(sp activation generate (alkyl)‐palladacycles, which can be captured by α ‐bromoacrylic acids afford tricyclic fused pyridinediones. addition, strategy also applied indole‐tethered construct pentacyclic pyridinediones via suquential Heck dearomatization/C(sp activation/decarboxylative cyclization. Notably, removal in reaction build interesting skeleton containing four‐membered ring. Preliminary mechanistic experiments indicate that five‐membered serve as key intermediates. Meanwhile, density functional theory (DFT) calculations provided insights into pathway.

Language: Английский

Citations

0

Creating glycoside diversity through stereoselective carboboration of glycals DOI Creative Commons

Zhenpeng Shen,

Yue Yu, Donghai Wu

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Nov. 23, 2024

Site-specific modification of glycosides to enhance or alter the physiological properties parent molecule has become a highly attractive strategy in drug development. However, creating glycoside building blocks with multiple diversifiable positions from readily available sugar precursors remains challenging task. Herein, we present regio- and stereoselective nickel-catalyzed carboboration glycals, which offers platform for generating diversity diverse C1 C2 potential. Specially, integration modifiable boronate group at position markedly amplifies versatility this approach, furnishing universal method swiftly rare sugars C2-site modifications through expedited downstream transformations. This demonstrates broad substrate scope tolerates various functional groups complex natural molecular architectures. Moreover, illustrate synthetic potential synthesis array analogs both products pharmaceuticals. Creating authors

Language: Английский

Citations

0