Visible-Light-Mediated Synthesis of C-Alkyl Glycosides via Glycosyl Radical Addition and Aryl Migration DOI

Rui-Qiang Jiao,

Yanan Ding,

Ming Li

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(33), P. 6099 - 6104

Published: Aug. 14, 2023

A visible-light-induced glycoarylation of activated olefins has been accomplished. Glycosyl radicals are generated via radical transfer strategies between (TMS)3SiOH and glycosyl bromides. Subsequent translocation rapid 1,4-aryl migration form β-sugar amide derivatives, eight types sugars compatible with this reaction. Further, the cascade reaction produced a quaternary carbon center good functional group adaptability high regioselectivity in mild conditions.

Language: Английский

Palladium Hydride-Enabled Hydroalkenylation of Strained Molecules DOI
Ziyan Zhang, Vladimir Gevorgyan

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(45), P. 20875 - 20883

Published: Oct. 31, 2022

We report the first palladium hydride enabled hydroalkenylation of strained molecules. This new mild protocol proceeds via a regio- and chemoselective hydropalladation step, followed by photoinduced radical alkyl Heck reaction. methodology represents reactivity mode for molecules opens avenues catalysis. The reaction is compatible with wide range functional groups can be applied to complex structures, delivering diverse array highly valuable modifiable alkenylated cyclobutanes cyclopropanes. A hydroalkenylation/diastereoselective rearrangement cascade toward cyclopentene scaffold has also been demonstrated.

Language: Английский

Citations

76

Diversification of Glycosyl Compounds via Glycosyl Radicals DOI Creative Commons
Yi Jiang, Yijun Zhang,

Boon Chong Lee

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(38)

Published: June 7, 2023

Glycosyl radical functionalization is one of the central topics in synthetic carbohydrate chemistry. Recent advances metal-catalyzed cross-coupling chemistry and metallaphotoredox catalysis provided powerful platforms for glycosyl diversification. In particular, discovery new precursors conjunction with these advanced reaction technologies have significantly expanded space compound synthesis. this Review, we highlight most recent progress area starting from 2021, reports included will be categorized based on different types better clarity.

Language: Английский

Citations

67

Photocoupled Electroreduction of CO2 over Photosensitizer-Decorated Covalent Organic Frameworks DOI

Qiu‐Jin Wu,

Duan‐Hui Si,

Shihua Ye

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(36), P. 19856 - 19865

Published: Aug. 31, 2023

Introducing an external visible-light field would be a promising strategy to improve the activity of electrocatalytic CO2 reduction reaction (CO2RR), but it still remains challenge due short excited-state lifetime active sites. Herein, Ru(bpy)3Cl2 struts as powerful photosensitive donors were immobilized into backbones Co-porphyrin-based covalent organic frameworks (named Co-Bpy-COF-Rux, x is molar ratio Ru and Co species, = 1/2 2/3) via coordination bonds, for photo-coupled CO2RR produce CO. The optimal Co-Bpy-COF-Ru1/2 displays high CO Faradaic efficiency 96.7% at -0.7 V vs reversible hydrogen electrode (RHE) partial current density 16.27 mA cm-2 -1.1 RHE under assistance light, both which far surpassing values observed in dark. significantly enhanced mainly attributed incorporation donor with long concomitantly giant built-in electric Co-Bpy-COF-Ru1/2, efficiently accelerate photo-induced electron transfer from cobalt-porphyrin light. Thus, sites have longer lower rate-determining steps' energy occurring during actual process. This first work porphyrin-based COFs CO2RR, opening new frontier construction efficient electrocatalysts.

Language: Английский

Citations

56

Recent Advances in Visible Light Induced Palladium Catalysis DOI
Sumon Sarkar, Kelvin Pak Shing Cheung, Vladimir Gevorgyan

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(9)

Published: Nov. 14, 2023

Visible light-induced Pd catalysis has emerged as a promising subfield of photocatalysis. The hybrid nature radical species enabled wide array radical-based transformations otherwise challenging or unknown via conventional chemistry. In parallel to the ongoing pursuit alternative, readily available precursors, notable discoveries have demonstrated that photoexcitation can alter not only oxidative addition but also other elementary steps. This Minireview highlights recent progress in this area.

Language: Английский

Citations

50

Transformations of carbohydrate derivatives enabled by photocatalysis and visible light photochemistry DOI Creative Commons

Daniel J. Gorelik,

Shrey P. Desai,

Sofia Jdanova

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(4), P. 1204 - 1236

Published: Jan. 1, 2024

This review article highlights the diverse ways in which recent developments areas of photocatalysis and visible light photochemistry are impacting synthetic carbohydrate chemistry.

Language: Английский

Citations

32

A review on sustainable iron oxide nanoparticles: syntheses and applications in organic catalysis and environmental remediation DOI
Dinesh S. Chaudhari, Rohit P. Upadhyay,

Gajanan Y. Shinde

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(13), P. 7579 - 7655

Published: Jan. 1, 2024

In this review paper, recent developments of iron oxide nanoparticles are highlighted and discussed in the field organic catalysis environmental remediation.

Language: Английский

Citations

28

Direct Formation of Amide-Linked C-Glycosyl Amino Acids and Peptides via Photoredox/Nickel Dual Catalysis DOI
Xiang-Yu Ye, Guanjie Wang, Zhichao Jin

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(8), P. 5502 - 5510

Published: Feb. 15, 2024

Glycoproteins account for numerous biological processes including those associated with diseases and infections. The advancement of glycopeptides has emerged as a promising strategy unraveling pathways discovering novel medicines. In this arena, key challenge arises from the absence efficient synthetic strategies to access glycoproteins. Here, we present highly concise approach bridging saccharides amino acids peptides through an amide linkage. Our amide-linked C-glycosyl are synthesized cooperative Ni-catalyzed photoredox processes. catalytic process generates glycosyl radical carbonyl radical, which subsequently combine yield products. saccharide reaction partners encompass mono-, di-, trisaccharides. All 20 natural acids, peptides, their derivatives can efficiently undergo glycosylations yields ranging acceptable high, demonstrating excellent stereoselectivities. As substantial expansion applications, have shown that simple function versatile building units constructing C-glycopeptides intricate spatial complexities.

Language: Английский

Citations

26

Application of the Spin-Center Shift in Organic Synthesis DOI Creative Commons
Feng‐Lian Zhang, Bin Li, K. N. Houk

et al.

JACS Au, Journal Year: 2022, Volume and Issue: 2(5), P. 1032 - 1042

Published: April 11, 2022

Spin-center shift (SCS) is a radical process involving 1,2-radical translocation along with two-electron ionic movement, such as elimination of an adjacent leaving group. Such was initially observed in some important biochemical transformations, and the unique property has also attracted considerable interest synthetic chemistry. Experimental, kinetic, well computational studies have been performed, series useful transformations developed applied organic synthesis based on SCS processes last 20 years. This Perspective overview mechanism.

Language: Английский

Citations

49

Recent advances in transition-metal-catalyzed glycosyl cross-coupling reactions DOI Open Access

Anrong Chen,

Bo Yang, Zhenghong Zhou

et al.

Chem Catalysis, Journal Year: 2022, Volume and Issue: 2(12), P. 3430 - 3470

Published: Nov. 8, 2022

Language: Английский

Citations

46

Merging of Light/Dark Palladium Catalytic Cycles Enables Multicomponent Tandem Alkyl Heck/Tsuji–Trost Homologative Amination Reaction toward Allylic Amines DOI

Nikita Kvasovs,

Jian Fang, Fedor Kliuev

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(33), P. 18497 - 18505

Published: Aug. 9, 2023

A visible light-induced palladium-catalyzed homologative three-component synthesis of allylic amines has been developed. This protocol proceeds

Language: Английский

Citations

36