Mechanochemistry II
In recent years, the use of mechanical energy to promote chemical changes on matter has grown in popularity. As a result, the number of new mechanochemical reactions, particularly in the field of organic chemistry, has been increasing. Consequently, now there is a significant body of evidence suggesting that mechanochemistry holds promise to become a game-changer in chemical synthesis. In this second thematic issue on mechanochemistry, the Beilstein Journal of Organic Chemistry aims at providing its readership with an excellent collection or papers in the field of mechanochemistry ranging from mechanosynthesis of organic molecules, catalysis under mechanochemical conditions, mechanistic studies of mechanochemical transformations, polymer mechanochemistry, and much more.
- Full Research Paper
- Published 29 Mar 2019
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Figure 1: Biologically relevant molecules made, used or derivatized by mechanochemistry.
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Figure 2: Isomeric diacyl-sn-glycerols (DAGs).
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Scheme 1: Synthetic route to access protected DAGs; PG = protecting group.
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Scheme 2: Protection of glycidol (1) with TBDMSCl in the ball mill. MM = mixer mill, PBM = planetary ball mil...
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Scheme 3: Cobalt-catalyzed epoxide ring-opening in the ball mill.
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Scheme 4: Mechanosynthesis of DAGs 5.
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Scheme 5: Conjugation of DAG 5a with 7-hydroxycoumarin (9).
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Figure 3: UV−vis spectra of DAG 6a (dotted line) and conjugated DAGs 10a and 10a’ as a mixture (10a/10a’ 72:2...
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- Review
- Published 12 Apr 2019
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Figure 1: A generalized overview of coordination-driven self-assembly.
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Figure 2: Examples of self-assembly or self-sorting and subsequent substitution.
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Figure 3: Synthesis of salen-type ligand followed by metal-complex formation in the same pot [55].
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Figure 4: Otera’s solvent-free approach by which the formation of self-assembled supramolecules could be acce...
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Figure 5: Synthesis of a Pd-based metalla-supramolecular assembly through mechanochemical activation for C–H-...
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Figure 6: a) Schematic representation for the construction of a [2]rotaxane. b) Chiu’s ball-milling approach ...
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Figure 7: Mechanochemical synthesis of the smallest [2]rotaxane.
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Figure 8: Solvent-free mechanochemical synthesis of pillar[5]arene-containing [2]rotaxanes [61].
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Figure 9: Mechanochemical liquid-assisted one-pot two-step synthesis of [2]rotaxanes under high-speed vibrati...
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Figure 10: Mechanochemical (ball-milling) synthesis of molecular sphere-like nanostructures [63].
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Figure 11: High-speed vibration milling (HSVM) synthesis of boronic ester cages of type 22 [64].
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Figure 12: Mechanochemical synthesis of borasiloxane-based macrocycles.
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Figure 13: Mechanochemical synthesis of 2-dimensional aromatic polyamides.
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Figure 14: Nitschke’s tetrahedral Fe(II) cage 25.
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Figure 15: Mechanochemical one-pot synthesis of the 22-component [Fe4(AD2)6]4− 26, 11-component [Fe2(BD2)3]2− ...
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Figure 16: a) Subcomponent synthesis of catalyst and reagent and b) followed by multicomponent reaction for sy...
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Figure 17: A dynamic combinatorial library (DCL) could be self-sorted to two distinct products.
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Figure 18: Mechanochemical synthesis of dynamic covalent systems via thermodynamic control.
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Figure 19: Preferential formation of hexamer 33 under mechanochemical shaking via non-covalent interactions of...
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Figure 20: Anion templated mechanochemical synthesis of macrocycles cycHC[n] by validating the concept of dyna...
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Figure 21: Hydrogen-bond-assisted [2 + 2]-cycloaddition reaction through solid-state grinding. Hydrogen-bond d...
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Figure 22: Formation of the cage and encapsulation of [2.2]paracyclophane guest molecule in the cage was done ...
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Figure 23: Formation of the 1:1 complex C60–tert-butylcalix[4]azulene through mortar and pestle grinding of th...
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Figure 24: Formation of a 2:2 complex between the supramolecular catalyst and the reagent in the transition st...
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Figure 25: Halogen-bonded co-crystals via a) I···P, b) I···As, and c) I···Sb bonds [112].
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Figure 26: Transformation of contact-explosive primary amines and iodine(III) into a successful chemical react...
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Figure 27: Undirected C–H functionalization by using the acidic hydrogen to control basicity of the amines [114]. a...
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- Full Research Paper
- Published 23 Apr 2019
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Scheme 1: Fast trimethylene carbonate polymerization using a solvent-free ball-milling approach.
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Figure 1: IR thermometer images showing reactor temperatures at the end of the two individual ball-milling re...
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- Full Research Paper
- Published 21 May 2019
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Scheme 1: Catalyzed mechanochemical Knoevenagel condensation of fluorobenzaldehydes and malonodinitrile. The ...
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Figure 1: Comparison of XRPD pattern of malonodinitrile (2) and (p-fluorobenzylidene) malonodinitrile (3a). T...
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Figure 2: a) XRPD pattern of (p-fluorobenzylidene)malonodinitrile (3a) direct after the synthesis with differ...
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Figure 3: Mass spectra of the different products of 3a. Red: peak off the molecular ion [M + H]+ of piperidin...
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Figure 4: a) In situ XRPD pattern of the mechanochemical Knoevenagel condensation of 1a and 2 with 2 µL catal...
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Figure 5: Comparison of XRPD patterns of both polymorphs of the product 3a. Red: triclinic polymorph t3a. Blu...
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Figure 6: Results of multivariate data analysis of Raman spectra for 30 Hz milling experiments. Principal com...
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- Letter
- Published 22 May 2019
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Figure 1: A) Porphyrin structure and labelling system. B) Substituents in the ortho-position of the group att...
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Scheme 1: Steps leading to the formation of a porphyrin.
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Scheme 2: Mechanochemical synthesis of tetramesitylporphyrin.
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- Full Research Paper
- Published 24 May 2019
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Figure 1: A: Mechanochemical polymerization of BCMBP (4,4’-bis(chloromethyl)-1,1’-biphenyl) towards the porou...
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Figure 2: A: IR spectra of the monomer BCMBP and NG-HCP showing a decrease of the C–Cl vibration after the re...
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Figure 3: A: Evolution of pressure in the course of the reaction measured by the GTM system. The addition of ...
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Figure 4: The correlation between the liquids’ boiling point and the SSA of the polymer. In general, a lower ...
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Figure 5: Physisorption isotherms of benzene vapour at different temperatures on HCP synthesised classically ...
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Figure 6: Physisorption isotherms of cyclohexane on mechanochemically synthesised HCP at temperatures 288, 29...
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