Energy-transfer-enabled photocatalytic transformations of aryl thianthrenium salts DOI Creative Commons
Kai Sun, Chang Ge, Xiaolan Chen

et al.

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

Published: Nov. 8, 2024

Aryl thianthrenium salts are valuable in photocatalysis but traditionally require external electron donors for activation. This study introduces an energy transfer (EnT) strategy the activation of aryl using 2,3,4,5,6-penta(carbazol-9-yl)benzonitrile (5CzBN) as a metal-free photocatalyst, eliminating need donors. Utilizing this EnT approach, we achieve C-H deuteration arenes under visible light with CDCl

Language: Английский

Electroreduction strategy: a sustainable tool for the generation of aryl radicals DOI
Xiaoqing Xie,

Wei Zhou,

Ruchun Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4318 - 4342

Published: Jan. 1, 2024

This review primarily focuses on the generation of aryl radicals via an electroreduction strategy, and systematically elaborates synthetic applications, scope, limitations substrates.

Language: Английский

Citations

9

Radical Reactions in Organic Synthesis: Exploring in-, on-, and with-Water Methods DOI Creative Commons
Chryssostomos Chatgilialoglu, Sebastián Barata‐Vallejo, Thanasis Gimisis

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(3), P. 569 - 569

Published: Jan. 23, 2024

Radical reactions in water or aqueous media are important for organic synthesis, realizing high-yielding processes under non-toxic and environmentally friendly conditions. This overview includes (i) a general introduction to chemistry media, (ii) synthetic approaches in, on, with as well heterogeneous phases, (iii) of carbon-centered radicals (or deuterium oxide) activated through coordination various Lewis acids, (iv) photocatalysis (v) applications bioinspired by naturally occurring processes. A wide range chemical strategies different experimental conditions have been reviewed that lead functional group translocation transformation reactions, leading the preparation complex molecules. These results reveal how solvent/medium/reagent radical has matured over last two decades, further discoveries anticipated near future.

Language: Английский

Citations

8

Mechanical‐Force‐Induced Non‐spontaneous Dehalogenative Deuteration of Aromatic Iodides Enabled by Using Piezoelectric Materials as a Redox Catalyst DOI

Ruiling Qu,

Shan Wan, Xuemei Zhang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(28)

Published: April 30, 2024

Abstract The development of green and efficient deuteration methods is great significance for various fields such as organic synthesis, analytical chemistry, medicinal chemistry. Herein, we have developed a dehalogenative strategy using piezoelectric materials catalysts in solid‐phase system under ball‐milling conditions. This non‐spontaneous reaction induced by mechanical force. D 2 O can serve both deuterium source an electron donor the transformation, eliminating need additional stoichiometric exogenous reductants. A series (hetero)aryl iodides be transformed into deuterated products with high incorporation. method not only effectively overcomes existing synthetic challenges but also used labelling drug molecules derivatives. Bioactivity experiments molecule suggest that D‐ipriflavone enhances inhibitory effects on osteoclast differentiation BMDMs vitro .

Language: Английский

Citations

8

Electroreductive deuteroarylation of alkenes enabled by an organo-mediator DOI Creative Commons
Xinling Li, Jianfeng Zhou,

Weijie Deng

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(29), P. 11418 - 11427

Published: Jan. 1, 2024

An environmentally friendly electroreduction approach is disclosed for site-specific introduction of deuterium via anti-Markovnikov selective deuteroarylation alkenes and aryl iodides with bipyridine as a mediator D 2 O ‘D’ source.

Language: Английский

Citations

8

Magnesium/methanol-d1: a practical reductive deuteration system for the deuterium labeling of α,β-unsaturated esters, nitriles and amides DOI

Penghui Ma,

J. Q. Li,

Lei Sun

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The use of magnesium and methanol in the reduction various functional groups has been well established. In this study, we present a reductive deuteration system using Mg/CH

Language: Английский

Citations

1

Access to N-α-deuterated amino acids and DNA conjugates via Ca(II)-HFIP-mediated reductive deutero-amination of α-oxo-carbonyl compounds DOI Creative Commons
Haoran Li,

Yuwei Liu,

Silin Zhang

et al.

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

Published: Feb. 20, 2025

The development of practical and selective strategies for deuterium incorporation to construct deuterated molecules, particularly deuterium-labeled amino acids, has become as a growing focus basic research, yet it remains formidable challenge. Herein, we present bioinspired calcium-HFIP-mediated site-selective reductive deutero-amination α-oxo-carbonyl compounds with amines. Utilizing d2-Hantzsch ester the source, this reaction attains remarkable deuteration efficiency (> 99% deuteration). It enables synthesis N-α-deuterated acid motifs wide range functionality, evidenced by over 130 examples. method exhibits compatibility diverse substrates, such peptides, drug natural products bearing different substituents. Moreover, application strategy in DNA-tagged acids/peptides been demonstrated. This work offers an efficient innovative solution chemistry holds substantial potential organic synthesis, medicinal chemistry, chemical biology.

Language: Английский

Citations

1

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures DOI
Han Liu, Lei Wang, Jin‐Tao Yu

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(5)

Published: April 8, 2023

Abstract Ring‐fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction such from readily available substrates becomes an important researching topic organic synthesis. Triggered by addition radicals to (activated or unactivated) double bonds alkenes, subsequent intramolecular addition/cyclization leads compounds. Following this procedure, variety functionalized ring‐fused were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, operational simple approaches toward versatile alkene‐based substrates. Here, we summarized recent on formation via radical‐triggered cascade reactions alkenes. Construction with no less than 3 fused rings developed during last decade included Review, corresponding mechanisms also discussed.

Language: Английский

Citations

22

Recent advances in the photocatalytic synthesis of aldehydes DOI
Yi Wang, Xiaofei Liu, Wei‐Min He

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(16), P. 4198 - 4210

Published: Jan. 1, 2023

This review summarizes the recently developed photocatalytic strategies for installation of formyl group into various scaffolds.

Language: Английский

Citations

19

Electrocatalytic Hydrogenation Using Palladium Membrane Reactors DOI Creative Commons
Guan‐Qun Han, Guodong Li, Yujie Sun

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(2), P. 328 - 343

Published: Jan. 29, 2024

Hydrogenation is a crucial chemical process employed in myriad of industries, often facilitated by metals such as Pd, Pt, and Ni catalysts. Traditional thermocatalytic hydrogenation usually necessitates high temperature elevated pressure, making the energy intensive. Electrocatalytic offers an alternative but suffers from issues competing H

Language: Английский

Citations

8

Hydrodeuteroalkylation of Unactivated Olefins Using Thianthrenium Salts DOI
Jie Zhang,

Mengjie Jiao,

Zheng Lu

et al.

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

Published: June 13, 2024

Isotopically labeled alkanes play a crucial role in organic and pharmaceutical chemistry. While some deuterated methylating agents are readily available, the limited accessibility of other deuteroalkyl reagents has hindered synthesis corresponding products. In this study, we introduce nickel-catalyzed system that facilitates various deuterium-labeled through hydrodeuteroalkylation d2-labeled alkyl TT salts with unactivated alkenes. Diverging from traditional reagents, thianthrenium (TT) can effectively selectively deuterium at α position chains using D

Language: Английский

Citations

6