Temperature‐Controlled Mechanochemistry for the Nickel‐Catalyzed Suzuki–Miyaura‐Type Coupling of Aryl Sulfamates via Ball Milling and Twin‐Screw Extrusion.** DOI
Robert R. A. Bolt, Sarah E. Raby‐Buck,

Katharine Ingram

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(44)

Published: Sept. 9, 2022

Abstract The use of temperature‐controlled mechanochemistry to enable the mechanochemical nickel‐catalyzed Suzuki–Miyaura coupling is herein described. Transitioning from a capricious room‐temperature protocol, through heated, PID‐controlled programmable jar heater manifold was required deliver an efficient method for aryl sulfamates (derived ubiquitous phenols) and boronic acid species. Furthermore, this process conducted using base‐metal nickel catalyst, in absence bulk solvent, air/moisture sensitive reaction set‐ups. This methodology showcased translation large‐scale twin‐screw extrusion enabling 200‐fold scale increase, producing decagram quantities C−C coupled material.

Language: Английский

Sustainability Assessment of Mechanochemistry by Using the Twelve Principles of Green Chemistry DOI
Karen J. Ardila‐Fierro, José G. Hernández

ChemSusChem, Journal Year: 2021, Volume and Issue: 14(10), P. 2145 - 2162

Published: April 9, 2021

In recent years, mechanochemistry has been growing into a widely accepted alternative for chemical synthesis. addition to their efficiency and practicality, mechanochemical reactions are also recognized sustainability. The association between Green Chemistry often originates from the solvent-free nature of most protocols, which can reduce waste production. However, satisfies more than one Principles Chemistry. this Review we will present series examples that clearly illustrate how significantly contribute fulfillment in holistic manner.

Language: Английский

Citations

462

Liquid‐Assisted Grinding Mechanochemistry in the Synthesis of Pharmaceuticals DOI

Ping Ying,

Jingbo Yu, Weike Su

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(5), P. 1246 - 1271

Published: Jan. 21, 2021

Abstract Mechanochemical reactions by milling, grinding or other types of mechanical action have emerged as a salient green approach because its wide applications towards academic and industrial chemical communities in sustainable solvent‐free/solvent‐less processes. Liquid‐assisted (LAG) an extension traditional solvent‐free mechanochemical techniques which small amount liquid is used additive to enhance and/or control reactivity, has been fruitfully applied the screening inclusion compounds, cocrystals, salts, solvates, polymorphs. However, utilization this important technique synthesis pharmaceutically biologically relevant targets was not adequately investigated. This review article summarizes overview latest development LAG approaches active pharmaceutical ingredients (API) drug‐like fragments, highlights superiority versus conventional syntheses. magnified image

Language: Английский

Citations

250

Mechanochemical Cross-Coupling Reactions DOI Creative Commons
Koji Kubota, Hajime Ito

Trends in Chemistry, Journal Year: 2020, Volume and Issue: 2(12), P. 1066 - 1081

Published: Oct. 20, 2020

Language: Английский

Citations

187

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

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

Mechanoredox Chemistry as an Emerging Strategy in Synthesis DOI
Jamie A. Leitch, Duncan L. Browne

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(38), P. 9721 - 9726

Published: April 1, 2021

Abstract Recent research endeavors have established that the mechanochemical activation of piezoelectric materials can open new avenues in redox chemistry. Impact forces, such as those imparted by a ball mill, been shown to transform barium titanate (BaTiO 3 ) into highly polarized state, which then donate an electron suitable oxidant and receive from reductant, mimicking photoredox catalytic cycles. Proof‐of‐concept studies elucidated mechanoredox chemistry holds great potential sustainable efficient radical‐based synthesis.

Language: Английский

Citations

112

A guide to direct mechanocatalysis DOI Creative Commons
Suhmi Hwang, Sven Grätz, Lars Borchardt

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(11), P. 1661 - 1671

Published: Jan. 1, 2022

Direct mechanocatalysis (DM) describes solvent-free catalytic reactions that are initiated by mechanical forces in mechanochemical reactors such as ball mills. The distinctive feature of DM is the milling materials,

Language: Английский

Citations

104

Mechanochemistry Can Reduce Life Cycle Environmental Impacts of Manufacturing Active Pharmaceutical Ingredients DOI
Or Galant,

Giacomo Cerfeda,

Aaron S. McCalmont

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2022, Volume and Issue: 10(4), P. 1430 - 1439

Published: Jan. 20, 2022

The scale-up of mechanochemical methods could play a transformative role in making manufacturing processes the pharmaceutical industry greener by eliminating solvent use and recovery. Combined with energy-efficient continuous processing that consolidates reaction steps, mechanochemistry's environmental economic benefits may translate across product supply chains. Here, we evaluate numerous sustainability green chemistry metrics for producing nitrofurantoin, an active ingredient (API), via twin-screw extrusion (TSE) conventional solvent-batch synthesis methods. We find significant reduction all TSE including energy, climate change, human ecological health, as well cost due to reducing excess reactant consumption solvents while maintaining high selectivity. In addition, replacing direct energy source drive chemical from mostly thermal electrical sources does not increase net life cycle consumed produce functionally equivalent API. conclude holds multiple APIs potentially other products.

Language: Английский

Citations

84

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