DDQ in mechanochemical C–N coupling reactions
- Shyamal Kanti Bera,
- Rosalin Bhanja and
- Prasenjit Mal
Beilstein J. Org. Chem. 2022, 18, 639–646, doi:10.3762/bjoc.18.64
Graphical Abstract
Figure 1: Our work on mechanochemical C–N coupling reactions using DDQ. The newly formed C–N bonds are shown ...
Figure 2: Scope of the mechanochemical synthesis of substituted benzimidazoles.
Figure 3: Synthesis of quinazolin-4(3H)-one derivatives.
Figure 4: The substrate scope for the synthesis of quinazolin-4(3H)-one derivatives.
Figure 5: a) Control experiment and b) Plausible mechanism.
Figure 6: Large-scale synthesis. a) 1,2-Disubstituted benzimidazoles. b) Substituted quinazolin-4(3H)-ones. R...
Mechanochemistry of supramolecules
- Anima Bose and
- Prasenjit Mal
Beilstein J. Org. Chem. 2019, 15, 881–900, doi:10.3762/bjoc.15.86
Graphical Abstract
Figure 1: A generalized overview of coordination-driven self-assembly.
Figure 2: Examples of self-assembly or self-sorting and subsequent substitution.
Figure 3: Synthesis of salen-type ligand followed by metal-complex formation in the same pot [55].
Figure 4: Otera’s solvent-free approach by which the formation of self-assembled supramolecules could be acce...
Figure 5: Synthesis of a Pd-based metalla-supramolecular assembly through mechanochemical activation for C–H-...
Figure 6: a) Schematic representation for the construction of a [2]rotaxane. b) Chiu’s ball-milling approach ...
Figure 7: Mechanochemical synthesis of the smallest [2]rotaxane.
Figure 8: Solvent-free mechanochemical synthesis of pillar[5]arene-containing [2]rotaxanes [61].
Figure 9: Mechanochemical liquid-assisted one-pot two-step synthesis of [2]rotaxanes under high-speed vibrati...
Figure 10: Mechanochemical (ball-milling) synthesis of molecular sphere-like nanostructures [63].
Figure 11: High-speed vibration milling (HSVM) synthesis of boronic ester cages of type 22 [64].
Figure 12: Mechanochemical synthesis of borasiloxane-based macrocycles.
Figure 13: Mechanochemical synthesis of 2-dimensional aromatic polyamides.
Figure 14: Nitschke’s tetrahedral Fe(II) cage 25.
Figure 15: Mechanochemical one-pot synthesis of the 22-component [Fe4(AD2)6]4− 26, 11-component [Fe2(BD2)3]2− ...
Figure 16: a) Subcomponent synthesis of catalyst and reagent and b) followed by multicomponent reaction for sy...
Figure 17: A dynamic combinatorial library (DCL) could be self-sorted to two distinct products.
Figure 18: Mechanochemical synthesis of dynamic covalent systems via thermodynamic control.
Figure 19: Preferential formation of hexamer 33 under mechanochemical shaking via non-covalent interactions of...
Figure 20: Anion templated mechanochemical synthesis of macrocycles cycHC[n] by validating the concept of dyna...
Figure 21: Hydrogen-bond-assisted [2 + 2]-cycloaddition reaction through solid-state grinding. Hydrogen-bond d...
Figure 22: Formation of the cage and encapsulation of [2.2]paracyclophane guest molecule in the cage was done ...
Figure 23: Formation of the 1:1 complex C60–tert-butylcalix[4]azulene through mortar and pestle grinding of th...
Figure 24: Formation of a 2:2 complex between the supramolecular catalyst and the reagent in the transition st...
Figure 25: Halogen-bonded co-crystals via a) I···P, b) I···As, and c) I···Sb bonds [112].
Figure 26: Transformation of contact-explosive primary amines and iodine(III) into a successful chemical react...
Figure 27: Undirected C–H functionalization by using the acidic hydrogen to control basicity of the amines [114]. a...
The mechanochemical synthesis of quinazolin-4(3H)-ones by controlling the reactivity of IBX
- Md Toufique Alam,
- Saikat Maiti and
- Prasenjit Mal
Beilstein J. Org. Chem. 2018, 14, 2396–2403, doi:10.3762/bjoc.14.216
Graphical Abstract
Figure 1: a) Explosion was observed when an arylamine was mixed with aldehydes in the presence of IBX. b) Ben...
Figure 2: Comparison of the current work with the existing literature reports.
Figure 3: Synthesis of quinazolin-4(3H)-one derivatives from the reaction of 1 with liquid aldehydes. aYields...
Figure 4: Synthesis of quinazolin-4(3H)-one derivatives from reaction of 1 and solid aldehydes. aYields with ...
Figure 5: Crystal structure of 3a (CCDC No. 1823611).
Figure 6: Plausible mechanism for the quinazolin-4(3H)-ones synthesis using IBX.
Scheme 1: Large scale synthesis of 3a.
Mechanochemical synthesis of small organic molecules
- Tapas Kumar Achar,
- Anima Bose and
- Prasenjit Mal
Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186
Graphical Abstract
Scheme 1: Mechanochemical aldol condensation reactions [48].
Scheme 2: Enantioselective organocatalyzed aldol reactions under mechanomilling. a) Based on binam-(S)-prolin...
Scheme 3: Mechanochemical Michael reaction [51].
Scheme 4: Mechanochemical organocatalytic asymmetric Michael reaction [52].
Scheme 5: Mechanochemical Morita–Baylis–Hillman (MBH) reaction [53].
Scheme 6: Mechanochemical Wittig reactions [55].
Scheme 7: Mechanochemical Suzuki reaction [56].
Scheme 8: Mechanochemical Suzuki–Miyaura coupling by LAG [57].
Scheme 9: Mechanochemical Heck reaction [59].
Scheme 10: a) Sonogashira coupling under milling conditions. b) The representative example of a double Sonogas...
Scheme 11: Copper-catalyzed CDC reaction under mechanomilling [67].
Scheme 12: Asymmetric alkynylation of prochiral sp3 C–H bonds via CDC [68].
Scheme 13: Fe(III)-catalyzed CDC coupling of 3-benzylindoles [69].
Scheme 14: Mechanochemical synthesis of 3-vinylindoles and β,β-diindolylpropionates [70].
Scheme 15: Mechanochemical C–N bond construction using anilines and arylboronic acids [78].
Scheme 16: Mechanochemical amidation reaction from aromatic aldehydes and N-chloramine [79].
Scheme 17: Mechanochemical CDC between benzaldehydes and benzyl amines [81].
Scheme 18: Mechanochemical protection of -NH2 and -COOH group of amino acids [85].
Scheme 19: Mechanochemical Ritter reaction [87].
Scheme 20: Mechanochemical synthesis of dialkyl carbonates [90].
Scheme 21: Mechanochemical transesterification reaction using basic Al2O3 [91].
Scheme 22: Mechanochemical carbamate synthesis [92].
Scheme 23: Mechanochemical bromination reaction using NaBr and oxone [96].
Scheme 24: Mechanochemical aryl halogenation reactions using NaX and oxone [97].
Scheme 25: Mechanochemical halogenation reaction of electron-rich arenes [88,98].
Scheme 26: Mechanochemical aryl halogenation reaction using trihaloisocyanuric acids [100].
Scheme 27: Mechanochemical fluorination reaction by LAG method [102].
Scheme 28: Mechanochemical Ugi reaction [116].
Scheme 29: Mechanochemical Passerine reaction [116].
Scheme 30: Mechanochemical synthesis of α-aminonitriles [120].
Scheme 31: Mechanochemical Hantzsch pyrrole synthesis [121].
Scheme 32: Mechanochemical Biginelli reaction by subcomponent synthesis approach [133].
Scheme 33: Mechanochemical asymmetric multicomponent reaction[134].
Scheme 34: Mechanochemical Paal–Knorr pyrrole synthesis [142].
Scheme 35: Mechanochemical synthesis of benzothiazole using ZnO nano particles [146].
Scheme 36: Mechanochemical synthesis of 1,2-di-substituted benzimidazoles [149].
Scheme 37: Mechanochemical click reaction using an alumina-supported Cu-catalyst [152].
Scheme 38: Mechanochemical click reaction using copper vial [155].
Scheme 39: Mechanochemical indole synthesis [157].
Scheme 40: Mechanochemical synthesis of chromene [158].
Scheme 41: Mechanochemical synthesis of azacenes [169].
Scheme 42: Mechanochemical oxidative C-P bond formation [170].
Scheme 43: Mechanochemical C–chalcogen bond formation [171].
Scheme 44: Solvent-free synthesis of an organometallic complex.
Scheme 45: Selective examples of mechano-synthesis of organometallic complexes. a) Halogenation reaction of Re...
Scheme 46: Mechanochemical activation of C–H bond of unsymmetrical azobenzene [178].
Scheme 47: Mechanochemical synthesis of organometallic pincer complex [179].
Scheme 48: Mechanochemical synthesis of tris(allyl)aluminum complex [180].
Scheme 49: Mechanochemical Ru-catalyzed olefin metathesis reaction [181].
Scheme 50: Rhodium(III)-catalyzed C–H bond functionalization under mechanochemical conditions [182].
Scheme 51: Mechanochemical Csp2–H bond amidation using Ir(III) catalyst [183].
Scheme 52: Mechanochemical Rh-catalyzed Csp2–X bond formation [184].
Scheme 53: Mechanochemical Pd-catalyzed C–H activation [185].
Scheme 54: Mechanochemical Csp2–H bond amidation using Rh catalyst.
Scheme 55: Mechanochemical synthesis of indoles using Rh catalyst [187].
Scheme 56: Mizoroki–Heck reaction of aminoacrylates with aryl halide in a ball-mill [58].
Scheme 57: IBX under mechanomilling conditions [8].
Scheme 58: Thiocarbamoylation of anilines; trapping of reactive aryl-N-thiocarbamoylbenzotriazole intermediate...
