Liquid-assisted vortex grinding supports the single-step solid-state construction of a [2.2]paracyclophane

Stojaković, Jelena; Farris, Brian S.; MacGillivray, Leonard R.

doi:10.1039/c4fd00006d

“… a) Catalytic photo‐mechanochemical [2+2] photodimerization; b) the vortex grinding set‐up for photo‐mechanochemistry; c) photo‐mechanical equipment by Štrukil et al . Panel (a) adapted from Ref.…”

Section: Light and Millingmentioning

confidence: 99%

Mechanochemistry for Synthesis

Friščić

¹

,

Mottillo

²

,

Titi

³

2019

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Mechanochemical solvent‐free reactions by milling, grinding or other types of mechanical action have emerged as a viable alternative to solution chemistry. Mechanochemistry offers not only a possibility to eliminate the need for bulk solvent use, and reduce the generation of waste, but it also unlocks the door to a different reaction environment in which synthetic strategies, reactions and molecules previously not accessible in solution, can be achieved. This Minireview examines the potential of mechanochemistry in chemical and materials synthesis, by providing a cross‐section of the recent developments in using ball milling for the formation of molecules and materials based on covalent and coordination bonds.

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“…Repeated grinding with additional olefin regenerated the photoactive cocrystal, permitting the reaction to be conducted with only a catalytic amount of resorcinol. Subsequently, the use of vortex grinding enabled simultaneous grinding and irradiation, enabling a catalytic photo‐mechanochemical route to cyclobutanes and p ‐cyclophanes (Figure a,b) …”

Section: Light and Millingmentioning

confidence: 99%

Mechanochemistry for Synthesis

Friščić

¹

,

Mottillo

²

,

Titi

³

2019

View full text Add to dashboard Cite

Mechanochemical solvent‐free reactions by milling, grinding or other types of mechanical action have emerged as a viable alternative to solution chemistry. Mechanochemistry offers not only a possibility to eliminate the need for bulk solvent use, and reduce the generation of waste, but it also unlocks the door to a different reaction environment in which synthetic strategies, reactions and molecules previously not accessible in solution, can be achieved. This Minireview examines the potential of mechanochemistry in chemical and materials synthesis, by providing a cross‐section of the recent developments in using ball milling for the formation of molecules and materials based on covalent and coordination bonds.

show abstract

“…In a recent Faraday discussion‐themed issue on “ Mechanochemistry: From Functional Solids to Single Molecules, ” the mechanochemistry of organic molecules, soft materials and pharmaceuticals, the mechanochemistry of inorganic compounds and coordination‐based materials, sonication and macromolecular mechanochemistry, current theoretical models for mechanochemical reactions, the mechanistic and kinetic understanding, catalysis, and scaling up of mechanochemistry were broadly discussed …”

Section: Introductionmentioning

confidence: 99%

Systematic studies on mechanochemical synthesis: Schiff bases from solid aromatic primary amines and aldehydes

Tigineh

¹

,

Liu

²

2019

J Chinese Chemical Soc

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A versatile and robust mechanochemical route to Aldehyde–Schiff base conversions has been established for a broad range of aldehydes via a simple cogrinding in mortar with a pestle under a solvent‐free, as well as solvent‐assisted, environment. The extent of amines reactivity under these conditions has also been explored, along with an examination of the possible connection between reactivity and electronic substituent effects. Results obtained demonstrated that the solvent‐free mechanochemical conversion of p‐toluidine and aromatic aldehydes to the corresponding Schiff bases proceeded more smoothly than the corresponding synthesis with 4‐aminobenzonitrile. The present approach not only provides good to excellent yields but also eliminates the disadvantages of the traditional synthesis of Schiff bases, such as the use of hazardous solvents, more or less demand of expensive catalysts, and looking for optimization on reaction conditions.

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Liquid-assisted vortex grinding supports the single-step solid-state construction of a [2.2]paracyclophane

Cited by 25 publications

References 18 publications

Mechanochemistry for Synthesis

Mechanochemistry for Synthesis

Mechanochemistry for Synthesis

Systematic studies on mechanochemical synthesis: Schiff bases from solid aromatic primary amines and aldehydes

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