Molecular Diversity, Journal Year: 2025, Volume and Issue: unknown
Published: April 10, 2025
Language: Английский
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(14)
Published: Jan. 5, 2024
Abstract Mechanochemical reactions offer methodological and environmental advantages for chemical synthesis, constantly attracting attention within the scientific community. Besides unmistakable sustainability advantages, conditions under which mechanochemical occur, namely solventless conditions, sometimes facilitate isolation of otherwise labile or inaccessible products. Despite these limited knowledge exists regarding mechanisms types intermediates involved. Nevertheless, in an expanding number cases, ex situ monitoring techniques have allowed observation, characterization, reaction transformations. In this Minireview, we present a series examples reactive been detected spanning organic, organometallic, inorganic, materials chemistry. Many were stabilized by non‐covalent interactions, played pivotal role guiding We believe that uncovering understanding such instances, growing mechanochemistry community could find novel opportunities catalysis discover new while achieving simplification design.
Language: Английский
Citations
28
Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(42)
Published: Aug. 28, 2023
Abstract The combination of a nickel(II) catalyst and mechanoredox under ball‐milling conditions promotes mechanical‐force‐driven C−N cross‐coupling reactions. In this nickel(II)/mechanoredox cocatalyst system, the modulation oxidation state nickel center, induced by piezoelectricity, is used to facilitate highly efficient aryl‐amination reaction, which characterized broad substrate scope, an inexpensive catalysts (NiBr 2 BaTiO 3 ), short reaction times, almost negligible quantity solvents. Moreover, can be readily up‐scaled multi‐gram scale, all synthetic operations carried out atmospheric without need for complicated setups. Furthermore, force‐induced system suitable excitation‐energy‐accepting molecules poorly soluble polyaromatic substrates that are incompatible with solution‐based nickel(II)/photoredox cocatalysts.
Language: Английский
Citations
32
Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(65)
Published: July 28, 2023
Here we describe the development of a sustainable and cost-effective approach for catalytic cross-coupling reactions in mechanochemistry. It is found that substrate's impact with vessel wall alone sufficient to initiate reaction, thus indicating milling balls function primarily as mixing agent direct mechanocatalytic Suzuki coupling. The absence can be offset by adjusting rheology using liquid-assisted grinding (LAG). LAG sweet spot 0.25 μL mg-1 confirmed both resonance acoustic mixers (RAMs) ball-free mixer mills, higher than presence balls. RAMs exhibit excellent performance achieving yields 90 % after 60 min complete conversion min. longevity significantly improved RAM, allowing at least 20 without deterioration.
Language: Английский
Citations
20
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(20)
Published: March 4, 2024
Abstract Birch reduction and similar dissolved metal‐type transformations hold significant importance in the organic synthesis toolbox. Historically, field has been dominated by alkali metal reductants. In this study, we report that largely neglected, low‐reactive alkaline earth metals can become powerful affordable reductants when used a ball mill under essentially solvent‐free conditions, presence of ethylenediamine THF as liquid additives. Calcium reduce both electron‐deficient electron‐rich arenes, with yields products to those obtained lithium metal. Magnesium reveals enhanced reducing power, enabling benzoic acids while keeping aromatic moieties intact allows for chemoselective transformations. The developed mechanochemical approach uses readily available safer‐to‐handle metals, operates air ambient temperature be gram‐scale preparations. Finally, demonstrate conditions other reductive transformations, including amination, deoxygenation, dehalogenation, alkene alkyne reductions.
Language: Английский
Citations
9
Molecular Catalysis, Journal Year: 2024, Volume and Issue: 559, P. 114087 - 114087
Published: April 1, 2024
Language: Английский
Citations
8
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(13), P. 9427 - 9439
Published: June 21, 2024
A mechanochemical synthesis of 1,2-disubstituted benzimidazoles from donor-acceptor cyclopropyl ketones and 1,2-diaminoarenes under metal-free solventless conditions is reported. The reaction does not require inert promoted by a stoichiometric amount 1,1,1,3,3,3-hexafluoroisopropanol. This cascade involves ring-opening, cyclization, retro-Mannich with aryl 1,2-diamines. Compared to its solution-phase counterpart, this approach shows fast reactivity (24 vs 1.5 h). Mechanistic investigations electrospray ionization mass spectrometry helped us propose the mechanism.
Language: Английский
Citations
8
RSC Mechanochemistry, Journal Year: 2024, Volume and Issue: 1(1), P. 38 - 42
Published: Jan. 1, 2024
α-Ketothioamides are formed by a mechanochemical solvent-free Willgeroth–Kindler-type reaction starting from acetophenone derivatives, amines, and elemental sulfur.
Language: Английский
Citations
7
ChemSusChem, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 17, 2025
Solvent-free techniques have gained considerable attention in recent years due to their environmental advantages and potential enable chemical reactivities beyond the reach of traditional solution-based methods. Mechanochemistry has emerged as a groundbreaking approach drive sustainable processes. Despite its promise, some challenges still need be explored, including overlooked issue material leaching during grinding, phenomenon which components from milling media or reaction vessels, such stainless steel, unintentionally alter outcomes. This study investigates role metal reducing arylnitrosamines by using poorly soluble solid reagent, thiourea dioxide (TDO), focusing on steel vessels. By comparing conventional mechanochemical methods with innovative solvent-free vibratory techniques, we assess extent contamination impact efficiency. These findings provide new insights into how influences processes offer valuable guidance for optimizing these forward-looking green methodologies.
Language: Английский
Citations
1
Green Chemistry, Journal Year: 2024, Volume and Issue: 26(14), P. 8341 - 8347
Published: Jan. 1, 2024
Resonant Acoustic Mixing (RAM) allows High Throughput Experimentation (HTE) using commercially available 96-well plates as exemplified by the nickel catalyzed C–N cross coupling of aryl halides with different amine and anilines.
Language: Английский
Citations
6
ACS Sustainable Chemistry & Engineering, Journal Year: 2023, Volume and Issue: 11(45), P. 16156 - 16164
Published: Oct. 27, 2023
A solid-state approach was used to synthesize compound PZ-1190, a multitarget ligand for serotonin and dopamine receptors with potential antipsychotic activity in rodents. Compared the classical batch synthesis approach, developed multistep mechanochemical protocol improved overall yield (from 32% 56%), reduced reaction time 42 4 h), decreased use of toxic reagents organic solvents. All synthesized intermediates PZ-1190 were isolated high purity by extraction without requirement chromatographic purification. obtained enantiomeric (≥99% ee) no impact grinding processes on integrity stereocenter. The described procedures represent rare examples reduction carboxylic function, which might open up possibility obtaining crucial β- γ-amino alcohols sustainable manner. oxidation an aliphatic alcohol into aldehyde using mechanochemistry has also been reported first time. results confirmed suitability as efficient method synthesizing candidates preclinical development.
Language: Английский
Citations
12