Rapid and scalable ruthenium catalyzed meta-C–H alkylation enabled by resonant acoustic mixing DOI Creative Commons
Arnab Dey, Rajesh Kancherla, Kuntal Pal

et al.

Communications Chemistry, Journal Year: 2024, Volume and Issue: 7(1)

Published: Dec. 18, 2024

Synthetic chemistry approaches for direct C–H bond alkylation offers a promising alternative to traditional functional-group-centered strategies which often involve multi-step procedures and may suffer from variety of challenges including scalability. Here, we introduce resonant mixing as an efficient method meta-C–H arenes using Ru-catalyst, avoiding the need bulk solvents, external temperature, or light. The described methodology is highly rapid, enabling multigram-scale synthesis meta-alkylation products within short reaction time achieving very high turnover frequency. operates via radical mechanism characterized by its mild conditions, substrate compatibility, exceptional meta-selectivity, all while significantly reducing times. authors acoustic Ru-catalyst mechanism,

Language: Английский

Green metrics in mechanochemistry DOI Creative Commons

Nicolas Fantozzi,

Jean‐Noël Volle, Andrea Porcheddu

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(19), P. 6680 - 6714

Published: Jan. 1, 2023

The quantitative assessment of the greenness mechanochemical processes for green metrics were calculated is herein reported. A general introduction to topic, variables influencing reaction outcome and, an outlook are also provided.

Language: Английский

Citations

81
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
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

47
Direct mechanocatalysis by resonant acoustic mixing (RAM) DOI Creative Commons
Cameron B. Lennox,

Tristan H. Borchers,

Lori Gonnet

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(27), P. 7475 - 7481

Published: Jan. 1, 2023

We demonstrate the use of a metal surface to directly catalyse copper-catalysed alkyne-azide click-coupling (CuAAC) reactions under conditions Resonant Acoustic Mixing (RAM) - recently introduced and scalable mechanochemical methodology that uniquely eliminates need for bulk solvent, as well milling media. By using simple copper coil catalyst, this work shows direct mechanocatalysis can occur in an impact-free environment, relying solely on high-speed mixing reagents against surface, without specially designed containers introducing experimental setup enables real-time Raman spectroscopy monitoring RAM processes, we 0th-order reaction kinetics several selected CuAAC reactions, supporting surface-based catalysis. The herein presented RAM-based is simple, effective one-pot, two-step synthesis triazoles

Language: Английский

Citations

35
Dual Nickel(II)/Mechanoredox Catalysis: Mechanical‐Force‐Driven Aryl‐Amination Reactions Using Ball Milling and Piezoelectric Materials DOI

Tamae Seo,

Koji Kubota, Hajime Ito

et al.

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

27
Synthesis without solvent: consequences for mechanochemical reactivity DOI Creative Commons
Lauren E. Wenger, Timothy P. Hanusa

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(96), P. 14210 - 14222

Published: Jan. 1, 2023

Solution-based reactions are a staple of synthetic chemistry—but what happens mechanochemically, when there is no solvent?

Language: Английский

Citations

21
Exploring Novel Synthetic Concepts and Strategies Using Mechanochemistry DOI
Koji Kubota

Bulletin of the Chemical Society of Japan, Journal Year: 2023, Volume and Issue: 96(9), P. 913 - 930

Published: Aug. 3, 2023

Abstract In the field of organic synthesis, a ball-milling synthetic technique has garnered significant attention in recent years as an eco-friendly and sustainable alternative to traditional solution-based methods. addition its environmental benefits, solid-state synthesis using mechanochemical protocols enables access novel areas chemical space that are unavailable by conventional reactions. this context, we interested designing developing new transformations based on unique reaction environment use mechanical forces ball mill. Account, highlight our latest findings concerning creation concepts strategies. These approaches harness distinctive mechanochemistry, rather than merely transferring well-established reactions from conditions.

Language: Английский

Citations

14
Halogen-bonded cocrystals via resonant acoustic mixing DOI Creative Commons
Alireza Nari, Jeffrey S. Ovens, David L. Bryce

et al.

RSC Mechanochemistry, Journal Year: 2024, Volume and Issue: 1(1), P. 50 - 62

Published: Jan. 1, 2024

Resonant acoustic mixing (RAM) is shown to be an effective mechanochemical method for producing halogen-bonded cocrystals, characterized here by X-ray diffraction and solid-state NMR. An elusive stoichiomorph unobtainable milling found via RAM.

Language: Английский

Citations

5
Sustainable click reactions: Use of greener reaction media in the synthesis of 1,2,3-triazoles DOI
Luan A. Martinho, Carlos Kleber Z. Andrade

Tetrahedron, Journal Year: 2024, Volume and Issue: 157, P. 133964 - 133964

Published: March 31, 2024

Language: Английский

Citations

5
Nickel-catalyzed cross-coupling aminations via high-throughput mechanochemistry enabled by resonant acoustic mixing DOI Creative Commons
Alice Nanni,

Deshen Kong,

Chen Zhu

et al.

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

5