Intramolecular direct arylation through mechanochemistry: efficient synthesis of corannulene-based peri-annulated curved nanographenes DOI
Zhongbo Zhang, Mihaiela C. Stuparu

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 6, 2025

Language: Английский

The mechanochemical synthesis of polymers DOI Creative Commons
Annika Krusenbaum, Sven Grätz, Getinet Tamiru Tigineh

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(7), P. 2873 - 2905

Published: Jan. 1, 2022

Mechanochemistry enables solvent-free syntheses of even novel polymer structures without the need monomer solubility.

Language: Английский

Citations

195

Mechanochemistry: New Tools to Navigate the Uncharted Territory of “Impossible” Reactions DOI Creative Commons
Federico Cuccu, Lidia De Luca, Francesco Delogu

et al.

ChemSusChem, Journal Year: 2022, Volume and Issue: 15(17)

Published: July 21, 2022

Mechanochemical transformations have made chemists enter unknown territories, forcing a different chemistry perspective. While questioning or revisiting familiar concepts belonging to solution chemistry, mechanochemistry has broken new ground, especially in the panorama of organic synthesis. Not only does it foster "thinking outside box", but also opened reaction paths, allowing overcome weaknesses traditional exactly where use well-established solution-based methodologies rules out progress. In this Review, reader is introduced an intriguing research subject not yet fully explored and waiting for improved understanding. Indeed, study mainly focused on that, although impossible solution, become possible under mechanochemical processing conditions, simultaneously entailing innovation expanding chemical space.

Language: Английский

Citations

184

Recent advances in n-type and ambipolar organic semiconductors and their multi-functional applications DOI
Yihan Zhang,

Yongshuai Wang,

Can Gao

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(4), P. 1331 - 1381

Published: Jan. 1, 2023

A comprehensive summary and deep insights into the synthesis, characterization multi-functional device applications of n-type ambipolar organic semiconductors are provided in this study.

Language: Английский

Citations

155

Advancing mechanochemical synthesis by combining milling with different energy sources DOI
Valentina Martinez, Tomislav Stolar, Bahar Karadeniz

et al.

Nature Reviews Chemistry, Journal Year: 2022, Volume and Issue: 7(1), P. 51 - 65

Published: Nov. 21, 2022

Language: Английский

Citations

145

Mechanochemical synthesis of magnesium-based carbon nucleophiles in air and their use in organic synthesis DOI Creative Commons
Rina Takahashi,

Anqi Hu,

Pan Gao

et al.

Nature Communications, Journal Year: 2021, Volume and Issue: 12(1)

Published: Nov. 18, 2021

Since the discovery of Grignard reagents in 1900, nucleophilic addition magnesium-based carbon nucleophiles to various electrophiles has become one most powerful, versatile, and well-established methods for formation carbon-carbon bonds organic synthesis. are typically prepared via reactions between halides magnesium metal a solvent. However, this method usually requires use dry solvents, long reaction times, strict control temperature, inert-gas-line techniques. Despite utility reagents, these requirements still represent major drawbacks from both an environmental economic perspective, often cause reproducibility problems. Here, we report general mechanochemical synthesis (Grignard paste form) air using ball milling technique. These can be used directly one-pot with nickel-catalyzed cross-coupling under solvent-free conditions.

Language: Английский

Citations

141

Continuous flow mechanochemistry: reactive extrusion as an enabling technology in organic synthesis DOI Creative Commons
Robert R. A. Bolt, Jamie A. Leitch, Andrew C. Jones

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(11), P. 4243 - 4260

Published: Jan. 1, 2022

Reactive extrusion provides a scale-up opportunity to turn mechanochemical process from ball-mill into continuous flow. This tutorial review summarises some of the early ground-breaking work in this area.

Language: Английский

Citations

113

Salient Achievements in Synthetic Organic Chemistry Enabled by Mechanochemical Activation DOI
Eusebio Juaristi, C.G. Ávila-Ortíz

Synthesis, Journal Year: 2023, Volume and Issue: 55(16), P. 2439 - 2459

Published: May 3, 2023

Abstract Although known for millennia, it is only recently that mechanochemistry has received serious attention by chemists. Indeed, during the past 15 years an extraordinary number of reports concerning solid-state chemical transformations through grinding and milling techniques have been recorded. This short review discusses circumstances led this renaissance, highlighting present intense interest in so-called green chemistry, enabling capacity to handle insoluble substrates, identification profound influence additives can on mechanochemically activated reactions. The core account focuses salient developments synthetic organic especially amino acid peptide­ mechanosynthesis, successful employment mechanochemical activation combination with asymmetric organocatalysis, promising enzymatic whole cell biocatalysis, remarkable achievement multicomponent selective reactions via complex, multistep reaction pathways, mechanosynthesis representative heterocycles. final section comments some pending tasks area, such as scaling-up processes be practical use industry, requirement easier more efficient control parameters monitoring devices, consequently careful analysis additional procedures a proper understanding phenomena. 1 Introduction 2 Brief History Mechanochemistry 3 Milling Equipment Reaction Parameters 4 Attributes That Propelled Its Present Renaissance 4.1 Enormous Attention Being Presently Paid Sustainable Chemistry 4.2 Reduced Energy Consumption 4.3 Additive-Based 4.4 Handling Insoluble Reactants 4.5 ‘Impossible’ Reactions Are Successful 4.6 Air- Water-Sensitive Reagents Ball 5 Salient Developments Mechanochemical Activation Synthetic Organic 5.1 Amino Acid Peptide Mechanosynthesis 5.2 Asymmetric Synthesis Organocatalysis under Ball-Milling Conditions 5.3 Mechanoenzymology 5.4 Multicomponent Activated 5.5 Heterocycles Modification 6 Future Directions 6.1 Scaling-Up Protocols 6.2 Temperature-Controlled 6.3 Understanding Transformations 6.4 Emerging Techniques 7 Conclusions

Language: Английский

Citations

52

Mechanochemistry-Directed Ligand Design: Development of a High-Performance Phosphine Ligand for Palladium-Catalyzed Mechanochemical Organoboron Cross-Coupling DOI

Tamae Seo,

Koji Kubota, Hajime Ito

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(12), P. 6823 - 6837

Published: March 9, 2023

Mechanochemical synthesis that uses transition-metal catalysts has attracted significant attention due to its numerous advantages, including low solvent waste, short reaction times, and the avoidance of problems associated with solubility starting materials. However, even though mechanochemical environment is largely different from homogeneous solution systems, catalysts, which were originally developed for use in solution, have been used directly reactions without any molecular-level modifications ensure their suitability mechanochemistry. Alas, this limited development more efficient cross-coupling processes. Here, we report a conceptually distinct approach, whereby mechanochemistry-directed design develop ligands Suzuki-Miyaura reactions. The ligand was guided by experimental observation catalyst deactivation via aggregation palladium species, problem particularly prominent solid-state By embedding into poly(ethylene glycol) (PEG) polymer, found phosphine-ligated palladium(0) species could be immobilized fluid phase created PEG chains, preventing physical mixing crystalline solid thus undesired deactivation. This catalytic system showed high activity polyaromatic substrates close room temperature. These usually require elevated temperatures reactive presence systems conventional such as SPhos. present study hence provides important insights high-performance potential inspire industrially attractive, almost solvent-free technologies.

Language: Английский

Citations

46

Tinkering with Mechanochemical Tools for Scale Up DOI Creative Commons
Javier F. Reynes, Valerio Isoni, Felipe Garcı́a

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(44)

Published: April 28, 2023

Mechanochemistry provides an environmentally benign platform to develop more sustainable chemical processes by limiting raw materials, energy use, and waste generation while using physically smaller equipment. A continuously growing research community has steadily showcased examples of beneficial mechanochemistry applications at both the laboratory preparative scale. In contrast solution-based chemistry, mechanochemical have not yet been standardized, thus scaling up is still a nascent discipline. The purpose this Minireview highlight similarities, differences challenges various approaches that successfully applied for range scales. We hope provide discussion starting point those interested in further developing commercial use and/or industrialisation.

Language: Английский

Citations

46

Mechanochemical Approach for Air‐Tolerant and Extremely Fast Lithium‐Based Birch Reductions in Minutes DOI
Yunpeng Gao, Koji Kubota, Hajime Ito

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(21)

Published: March 22, 2023

Birch reduction has been widely used in organic synthesis for over half a century as powerful method to dearomatize arenes into 1,4-cyclohexadiene derivatives. However, the conventional reaction using liquid ammonia requires laborious procedures ensure inert conditions and low temperatures. Although several ammonia-free modifications have reported, development of an operationally simple, efficient, scalable protocol remains challenge. Herein, we report lithium-based air without special operating ball-milling technique. This is characterized by its operational simplicity extremely short time (within 1 min), probably owing situ mechanical activation lithium metal, broad substrate scope, no requirement dry bulk solvents. The potential our flash also demonstrated efficient bioactive target molecules gram-scale synthesis.

Language: Английский

Citations

45