Photoinduced Transition‐MetalExternal Photosensitizer Free Benzylic Fluorination of Unactivated Alkylarenes DOI

Jiawen Lai,

Xuan Xiao,

Shixing Shao

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 20, 2024

A green and efficient protocol for the direct monofluorination of unactivated alkylarenes under visible-light irradiation has been developed, without any extraneous transition-metal catalysts or photosensitizers. This method is compatible with a broad spectrum functional groups, including carboxylic alcoholic scaffolds, mild reaction conditions. Gram-scale synthesis fluorine-containing pharmaceutical analogue was successfully executed, underscoring strategy's reliability practicality. Furthermore, mechanistic studies suggest that single-electron transfer mechanism might be responsible generation benzylic radicals in initiation step.

Language: Английский

Remote site-selective arene C–H functionalization enabled by N-heterocyclic carbene organocatalysis DOI
Qing‐Zhu Li,

Wen‐Lin Zou,

Zhaoyuan Yu

et al.

Nature Catalysis, Journal Year: 2024, Volume and Issue: 7(8), P. 900 - 911

Published: July 11, 2024

Language: Английский

Citations

17

Review of application of the I2 and dimethyl sulfoxide combined reagent system to aryl methyl ketones for diverse transformations DOI
Dongsheng Yang, Xiang‐Long Chen, An‐Xin Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2665 - 2692

Published: Jan. 1, 2024

The synthesis of small molecules and complex scaffolds is one the most important topics in organic synthesis.

Language: Английский

Citations

16

The green chemistry paradigm in modern organic synthesis DOI
Sergei G. Zlotin, Ksenia S. Egorova, Valentine P. Ananikov

et al.

Russian Chemical Reviews, Journal Year: 2023, Volume and Issue: 92(12), P. RCR5104 - RCR5104

Published: Dec. 1, 2023

After the appearance of green chemistry concept, which was introduced in vocabulary early 1990s, its main statements have been continuously developed and modified. Currently, there are 10–12 cornerstones that should form basis for an ideal chemical process. This review analyzes accumulated experience achievements towards design products processes reduce or eliminate use generation hazardous substances. The presents views leading Russian scientists specializing various fields this subject, including homogeneous heterogeneous catalysis, fine basic organic synthesis, electrochemistry, polymer chemistry, based on bio-renewable feedstocks energetic compounds materials. A new approach to quantitative evaluation environmental friendliness by authors is described. <br> bibliography includes 1761.

Language: Английский

Citations

39

Metal-free photoinduced hydrogen atom transfer assisted C(sp3)–H thioarylation DOI
Jagrit Grover, Gaurav Prakash, Chitrala Teja

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(9), P. 3431 - 3436

Published: Jan. 1, 2023

A mild metal-free approach for C(sp 3 )–H thioarylation of organic building blocks.

Language: Английский

Citations

24

Phototriggered Self-Catalyzed Phosphorylation of 3,4-Dihydroquinoxalin-2(1H)-ones with Diarylphosphine Oxides in EtOH DOI
Yanfang Jiang, Wen‐Tao Ouyang,

Hong‐Tao Ji

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 19, 2024

A highly effective external photocatalyst- and additive-free method for the phosphorylation of 3,4-dihydroquinoxalin-2(1

Language: Английский

Citations

12

An account on selective functionalization of C(sp3)-H bonds by oxidative cross dehydrogenative coupling (CDC) reactions under transition-metal free condition DOI

Sreya Gupta,

S. C. Pal

Sustainable Chemistry and Pharmacy, Journal Year: 2025, Volume and Issue: 44, P. 101955 - 101955

Published: Feb. 26, 2025

Language: Английский

Citations

1

Metal-Free Carbon-Based Nanomaterials: Insights from Synthesis to Applications in Sustainable Catalysis DOI
Vishal Bharati Jaryal, Alberto Villa, Neeraj Gupta

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2023, Volume and Issue: 11(41), P. 14841 - 14865

Published: Sept. 15, 2023

The development of cutting-edge catalysts is critical in material science for sustainable development. Though, metals have always been used catalysis enabling essential chemicals, but their use not considered owing to the high cost, toxicity, and poor durability. Nevertheless, modern focus has shifted towards metal free materials due leading role Carbon-based nanomaterials become researchers over last 30 years are either as a catalyst support or metal-free various chemical conversions. They highly anticipated state-of-the-art specific surface area, conductivity, tunable functional groups. This account summarizes strategies proposed by our group design carbon electrochemical sensing, biomass valorization, synthesis value-added chemicals. Also, "metal-free" point-of-care devices fabricated provide affordable healthcare services user end. designed using graphitic nitride, reduced graphene oxide, Janus 2D nanomaterials, ultradispersed diamonds, nanotubes. Their efficacy can be improved building composites with incorporating defects. Finally, we share some knowledge insights regarding current challenges future perspectives this emerging field.

Language: Английский

Citations

18

Minisci‐Type Carbamoylation of Azauracils with Oxamic Acids DOI
Changduo Pan, Dongdong Chen,

Miao Zeng

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(7)

Published: Jan. 19, 2024

Abstract A Minisci‐type carbamoylation of azauracils was developed to afford 6‐carbamoyl in yields up 94 %. In this transformation, oxamic acids were employed as the carbamoyl radical sources under metal‐free conditions. It features high atom economy, good functional group compatibility and convenient operation.

Language: Английский

Citations

5

Synthesis, Characterization, and Reactivity of a Highly Oxidative Mononuclear Manganese(IV)–Bis(Fluoro) Complex DOI
Donghyun Jeong,

Yujeong Lee,

Yuri Lee

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(6), P. 4172 - 4177

Published: Feb. 5, 2024

Recently, transition-metal terminal nonoxo complexes have shown a remarkable ability to activate and functionalize C–H bonds via proton-coupled electron transfer (PCET). Here we report the first example of mononuclear manganese(IV) bis(fluoro) complex bearing tetradentate pyridinophane ligand, [MnIV(TBDAP)(F)2]2+ (3), with an X-ray single crystal structure physicochemical characterization. The has very high reduction potential 1.61 V vs SCE, thereby enabling four-electron oxidation mesitylene 3,5-dimethylbenzaldehyde. Kinetic studies, including kinetic isotope effect employment other toluene derivatives, reveal (ET)-driven PCET in bond activation by 3. This novel metal halide intermediate would be prominently valuable for expanding chemistry.

Language: Английский

Citations

5

Hexafluoroisopropanol-assisted selective intramolecular synthesis of heterocycles by single-electron transfer DOI Creative Commons
Jiale Xie, Jiayu Zhang, Sitthichok Kasemthaveechok

et al.

Nature Synthesis, Journal Year: 2024, Volume and Issue: 3(8), P. 1021 - 1030

Published: July 1, 2024

Abstract Intramolecular amination of remote aliphatic C–H bonds via hydrogen-atom transfer reactions has become a powerful tool for accessing saturated nitrogen-containing heterocycles. However, the formation six-membered rings or oxa-heterocycles remains formidable challenge Hofmann–Löffler–Freytag reactions. Here we show how by simply combining bench-stable (bis(trifluoroacetoxy)iodo)benzene and hexafluoroisopropanol (HFIP) can switch from well-established mechanism to different versatile reaction pathway that enables selective C( sp 3 )–H bond functionalization. We have exploited facile radical cations single-electron transfer, in presence absence light, synthesize pyrrolidines piperidines, including drug-type molecules, along with O-heterocycles. Experimental computational mechanistic studies support two distinct pathways, depending on electron density substrate, which HFIP plays multifunctional role.

Language: Английский

Citations

5