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Search for "4,4’-bipyridine" in Full Text gives 9 result(s) in Beilstein Journal of Organic Chemistry.
On the photoluminescence in triarylmethyl-centered mono-, di-, and multiradicals
- Daniel Straub,
- Markus Gross,
- Mona E. Arnold,
- Julia Zolg and
- Alexander J. C. Kuehne
Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80
Graphical Abstract
Figure 1: a) Tris(trichlorophenyl)methyl (TTM) radical and related trityl radicals, b) HDMO, SOMO, LUMO orbit...
Figure 2: Mixed halide tri- and perhalogenated triphenylmethyl radicals: a) Molecular structures of homo- and...
Figure 3: Pyridine-functionalized triarylmethyl radicals. a) Chemical structures of X2PyBTM, Py2MTM, and Au-F2...
Figure 4: Pyridine-functionalized triarylmethyl radicals. a) Molecular structure of Mes2F2PyBTM, and b) its f...
Figure 5: Carbazole functionalized triarylmethyl radical. a) Chemical structure of Cz-BTM and b) its energy d...
Figure 6: Donor-functionalized triphenylmethyl radicals. Molecular structures of TTM-Cz, DTM-Cz, TTM-3PCz, PT...
Figure 7: Tuning of the donor strength. Functionalization with electron-donating and electron-withdrawing gro...
Figure 8: Tuning of the donor strength, by varying the Cz-derived donor (1–36) on a TTM radical fragment. a) ...
Figure 9: Three-state model and Marcus theory: q is the charge transfer coordinate and G the free energy. Gro...
Figure 10: Dendronized carbazole donors on TTM radicals. a) Molecular structures of G3TTM and G4TTM. b) Photol...
Figure 11: Electronic extension of the Cz donor. a) Molecular structures and optoelectronic properties of TTM-...
Figure 12: Kekulé diradicals: a) hexadeca- and perchlorinated Thiele (TTH, PTH), Chichibabin (TTM-TTM, PTM-PTM...
Figure 13: Non-Kekulé diradicals: perchlorinated Schlenk–Brauns radical (m-PTH), meta-coupled TTM radicals in ...
Figure 14: UV–vis absorption and photoluminescence spectra of a) TTH in solvents of different polarity, b) dir...
Figure 15: Molecular structures of m-4BTH (meta-butylated Thiele hydrocarbon), m-4TTH (meta-trichlorinated Thi...
Figure 16: a) Polystyrene-based TTM-Cz polymer. b) Molecular structure of radical particles with backbone thro...
Figure 17: Molecular structures of polyradicals. a) Molecular structures of p-TBr6Cl3M-F8, p-TBr6Cl3M-acF8 and ...
Figure 18: Structures of coordination and metal-organic frameworks. a) Carboxylic acid functionalized monomers...
Figure 19: Structures of coordination and metal-organic frameworks. a) Molecular structures of monomers TTMDI, ...
Figure 20: Molecular structures of covalent organic frameworks m-TPM-Ph-COF, m-PTM-Ph-COF, p-TPH-COF, p-PTH-COF...
Figure 21: Molecular structures of covalent organic frameworks PTMAc-COF, oxTAMAc-COF, TOTAc-COF, PTMTAz-COF, p...
Halogen-bonding-induced diverse aggregation of 4,5-diiodo-1,2,3-triazolium salts with different anions
- Xingyu Xu,
- Shiqing Huang,
- Zengyu Zhang,
- Lei Cao and
- Xiaoyu Yan
Beilstein J. Org. Chem. 2020, 16, 78–87, doi:10.3762/bjoc.16.10
- halogen acceptors was also investigated. Diffusion of ether into the mixture of 4,4'-bipyridine (bpy) and 2-BF4 in dichloromethane leads to the crystallization of 2-BF4·0.5bpy (Figure 8). It crystallizes in the monoclinic space group P21/c. The acceptor 4,4'-bipyridine provides a complementary link for 1D
- the former shows a boat conformation and the latter forms a rectangle conformation. Triazolium salts form a linear polymer with polyiodide. 2-BF4 forms co-crystals with 4,4'-bipyridine via halogen bonding. DFT calculation results show that the σ holes of 4,5-diiodo-1,2,3-triazolium is similar to the σ
- , 1.41, N, 2.67%; found: C, 15.93, H, 1.66, N, 2.41%. 2-BF4.0.5bpy: 2-BF4 (65 mg, 0.1 mmol) and 4,4'-bipyridine (16 mg, 0.1 mmol) was mixed in dichloromethane (4 mL) in a round bottom flask. The single crystals were obtained by slow diffusion of ether into a dichloromethane solution. Colourless solid, 28
Graphical Abstract
Figure 1: 1,2,3-Triazole based XB donors: 1,2,3-triazole A, 1,2,3-triazolium B, 1,2,3-triazolylidene C and di...
Scheme 1: Synthesis of 4,5-diiodo-1,3-dimesityl-1,2,3-triazolium with iodide, Mes: 2,4,6-Me3C6H2.
Scheme 2: Synthesis of 4,5-diiodo-1,3-dimesityl-1,2,3-triazolium with different anion.
Figure 2: Packing structure of 2-I (top), 2-Br (middle) and 2-Cl (bottom). Hydrogen atoms have been omitted f...
Figure 3: Packing structure of 2-BF4. Hydrogen atoms have been omitted for clarity.
Figure 4: Packing structure of 2-OAc. Hydrogen atoms and solvent molecules have been omitted for clarity.
Figure 5: Packing structure of 2-TFA. Hydrogen atoms and disorder of fluorine atoms have been omitted for cla...
Figure 6: Packing structure of 2-I.1.5I2. Hydrogen atoms have been omitted for clarity.
Figure 7: Packing structure of 2-I.3.5I2. Hydrogen atoms have been omitted for clarity.
Figure 8: Packing structure of 2-BF4.0.5bpy. Hydrogen atoms and dichloromethane have been omitted for clarity....
Figure 9: 1,2,3-Triazole-based halogen model calculation: electrostatic potential surfaces mapped on total de...
Complexation of 2,6-helic[6]arene and its derivatives with 1,1′-dimethyl-4,4′-bipyridinium salts and protonated 4,4'-bipyridinium salts: an acid–base controllable complexation
- Jing Li,
- Qiang Shi,
- Ying Han and
- Chuan-Feng Chen
Beilstein J. Org. Chem. 2019, 15, 1795–1804, doi:10.3762/bjoc.15.173
- reaction of 4,4′-bipyridine with concentrated HCl in acetonitrile followed by counteranion exchange with sodium tetrakis[3,5-di(trifluoromethyl)phenyl]borate (NaBArF) in dichloromethane. The new compounds were confirmed by NMR spectroscopy and high-resolution mass spectrometry (Supporting Information File
- solution. Acid–base controlled complexation between H2 and G4 4,4′-Bipyridine easily forms protonated 4,4′-pyridinium salts and vice versa. Hence we could conveniently control the association and dissociation of the host–guest complexes based on protonated 4,4′-pyridinium guests by use of acid and base. As
- shown in Figure 7, when 2.2 equiv of DBU were added into the solution of complex H2·G4 in CD2Cl2, the signals for protons 3 and 6 of complex H2·G4 disappeared while the proton signals of free H2 and 4,4'-bipyridine were observed, which indicated that the complex dissociated. On the other hand, when 2.2
Graphical Abstract
Figure 1: Structures and proton designations of hosts H1–5 and guests G1–4.
Scheme 1: Synthesis of hosts H3–5.
Figure 2: Partial 1H NMR spectra (400 MHz CDCl3/acetone-d6 1:2 (v/v), 298 K) of (a) free H1, (b) H1 with 1.0 ...
Figure 3: Partial 1H NMR spectra (400 MHz, CD2Cl2, 298 K) of (a) free H1, (b) H1 with 1.0 equiv G4, (c) free ...
Figure 4: Crystal structure of complex H1·G1. (a) Top view, (b) side view, and (c) packing viewed along c-axi...
Figure 5: Crystal structure of complex H5·G1. (a) Top view, (b) side view, and (c) packing viewed along the a-...
Figure 6: Calculated structures of the complexes at the B3LYP/6-31G level of theory. (a) Top view and (b) sid...
Figure 7: Schematic representation of the acid–base controlled complexation process and partial 1H NMR spectr...
Mechanochemistry of supramolecules
- Anima Bose and
- Prasenjit Mal
Beilstein J. Org. Chem. 2019, 15, 881–900, doi:10.3762/bjoc.15.86
- condition than in aqueous media [56]. When a 1:1 mixture of the platinum salt [(en)PtNO3)2] and 4,4'-bipyridine were grinded in a mortar and pestle for 10 min, an NMR yield of 76% was found for the formation of molecular square 8 (Figure 4a). Similar structures were reported by Fujita’s group [57] in which
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...
Host–guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies
- Rakesh Puttreddy,
- Ngong Kodiah Beyeh,
- S. Maryamdokht Taimoory,
- Daniel Meister,
- John F. Trant and
- Kari Rissanen
Beilstein J. Org. Chem. 2018, 14, 1723–1733, doi:10.3762/bjoc.14.146
- -oxide (3), 4-methylpyridine N-oxide (4), 2,6-dimethylpyridine N-oxide (5), 2-methoxypyridine N-oxide (6), 3-methoxypyridine N-oxide (7), 4-methoxypyridine N-oxide (8), 2,6-dimethoxypyridine N-oxide (9), 4-phenylpyridine N-oxide (10), 4,4'-bipyridine N,N'-dioxide (11) and 2,2'-bipyridine N,N'-dioxide (12
Graphical Abstract
Figure 1: The chemical structures of C-ethyl-2-bromoresorcinarene (BrC2), C-propyl-2-bromoresorcinarene (BrC3...
Figure 2: X-ray crystal structures of (a) 3@BrC6, (b) 4@BrC6, (c) 5@BrC6, (d) 6@BrC6, (e) 7@BrC6, (f) 8@BrC6,...
Figure 3: Comparison of X-ray crystal structures (a) 3@BrC2, (c) 3@BrC3, and (e) 3@BrC6 and their DFT-based o...
Figure 4: (a) The negative potential localised on the N-oxide oxygen in 3@BrC6 and, (b) the positive charge d...
Figure 5: An expansion of the 1H NMR (6.6 mM at 298 K, 500 MHz) of BrC6 complexes with 3. Spectra are produce...
A versatile route to polythiophenes with functional pendant groups using alkyne chemistry
- Xiao Huang,
- Li Yang,
- Rikard Emanuelsson,
- Jonas Bergquist,
- Maria Strømme,
- Martin Sjödin and
- Adolf Gogoll
Beilstein J. Org. Chem. 2016, 12, 2682–2688, doi:10.3762/bjoc.12.265
- quinone moieties are vulnerable in nucleophilic and acidic environments. Furthermore, the viologen moiety, available from 4,4’-bipyridine (BP) has potential for energy storage and electrochromic applications [35][36], but it has previously been anchored to a polymer backbone only by oxidative coupling via
- -bromoterephthalate and 2-bromo-4,4’-bipyridine were prepared according to reported procedures [38][39]. The electron acceptor phthalimide (PT) was attached to EDOT via cycloaddition between the alkyne and an alkylazide to produce derivative 13 (Scheme 4). Regioselective formation of 13 involved the Cu(I)-catalyzed
Graphical Abstract
Scheme 1: Previous and present EDOT functionalization routes.
Scheme 2: The synthetic route from glycidol to pyEDOT (3).
Scheme 3: The synthetic route from D-mannitol diketal to eEDOT 8 and TMS-eEDOT 8’.
Scheme 4: New EDOT derivatives 9–13 accessible from pyEDOT with bromo-pendant group precursors via Sonogashir...
Figure 1: CVs of electrochemical polymerization of (a) pyEDOT 3 and (b) EDOT in MeCN solution with 0.1 M TEAPF...
Figure 2: CVs of electrochemical polymerization of (a) pyEDOT-DeT (9), (b) pyEDOT-AQ (12) and (c) pyEDOT-MVPF...
Recent advances in copper-catalyzed C–H bond amidation
- Jie-Ping Wan and
- Yanfeng Jing
Beilstein J. Org. Chem. 2015, 11, 2209–2222, doi:10.3762/bjoc.11.240
- on this area from Truong et al. [75] showed that the heterogeneous and recyclable Cu2(BDC)2(BPY) catalyst (BDC = benzene- 1,4-dicarboxylate; BPY = 4,4′-bipyridine) could catalyze this kind of amidation reaction with excellent selectivity to provide ynamides. Another point was that the C–H bond could
Graphical Abstract
Scheme 1: Copper-catalyzed C–H amidation of tertiary amines.
Scheme 2: Copper-catalyzed C–H amidation and sulfonamidation of tertiary amines.
Scheme 3: Copper-catalyzed sulfonamidation of allylic C–H bonds.
Scheme 4: Copper-catalyzed sulfonamidation of benzylic C–H bonds.
Scheme 5: Copper-catalyzed sulfonamidation of C–H bonds adjacent to oxygen.
Scheme 6: Copper-catalyzed amidation and sulfonamidation of inactivated alkyl C–H bonds.
Scheme 7: Copper-catalyzed amidation and sulfonamidation of inactivated alkanes.
Scheme 8: Copper-catalyzed intramolecular C–H amidation for lactam synthesis.
Scheme 9: Copper-catalyzed intramolecular C–H amidation for lactam synthesis.
Scheme 10: Copper-catalyzed amidation/sulfonamidation of aryl C–H bonds.
Scheme 11: C–H amidation of pyridinylbenzenes and indoles.
Scheme 12: Mechanism of the Cu-catalyzed C2-amidation of indoles.
Scheme 13: Copper-catalyzed, 2-phenyl oxazole-assisted C–H amidation of benzamides.
Scheme 14: DG-assisted amidation/imidation of indole and benzene C–H bonds.
Scheme 15: Copper-catalyzed C–H amination/amidation of quinoline N-oxides.
Scheme 16: Copper-catalyzed aldehyde formyl C–H amidation.
Scheme 17: Copper-catalyzed formamide C–H amidation.
Scheme 18: Copper-catalyzed sulfonamidation of vinyl C–H bonds.
Scheme 19: CuCl2-catalyzed amidation/sulfonamidation of alkynyl C–H bonds.
Scheme 20: Cu(OH)2-catalyzed amidation/sulfonamidation of alkynyl C–H bonds.
Scheme 21: Sulfonamidation-based cascade reaction for the synthesis of tetrahydrotriazines.
Scheme 22: Copper-catalyzed cascade reaction for the synthesis of quinazolinones.
Scheme 23: Copper-catalyzed cascade reactions for the synthesis of fused quinazolinones.
Scheme 24: Copper-catalyzed synthesis of quinazolinones via methyl C–H bond amidation.
Scheme 25: Dicumyl peroxide-based cascade synthesis of quinazolinones.
Scheme 26: Copper-catalyzed cascade reactions for the synthesis of indolinones.
Cross-dehydrogenative coupling for the intermolecular C–O bond formation
- Igor B. Krylov,
- Vera A. Vil’ and
- Alexander O. Terent’ev
Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13
- ]. The coupling of aldehydes and formamides with 2-substituted phenols was carried out in the presence of heterogeneous catalysts, such as CuO on α-Fe2O3-modified carbon nanotubes (a magnetically separable catalyst) [158] and the metal-organic framework Cu2(4,4’-biphenyldicarboxylate)2(4,4’-bipyridine
Graphical Abstract
Scheme 1: Cross-dehydrogenative coupling.
Scheme 2: Cross-dehydrogenative C–O coupling.
Scheme 3: Regioselective ortho-acetoxylation of meta-substituted arylpyridines and N-arylamides.
Scheme 4: ortho-Acyloxylation and alkoxylation of arenes directed by pyrimidine, benzoxazole, benzimidazole a...
Scheme 5: Cu(OAc)2/AgOTf/O2 oxidative system in the ortho-alkoxylation of arenes.
Scheme 6: Pd(OAc)2/persulfate oxidative system in the ortho-alkoxylation and acetoxylation of arenes with nit...
Scheme 7: ortho-Acetoxylation and methoxylation of O-methyl aryl oximes, N-phenylpyrrolidin-2-one, and (3-ben...
Scheme 8: Ruthenium-catalyzed ortho-acyloxylation of acetanilides.
Scheme 9: Acetoxylation and alkoxylation of arenes with amide directing group using Pd(OAc)2/PhI(OAc)2 oxidat...
Scheme 10: Alkoxylation of azoarenes, 2-aryloxypyridines, picolinamides, and N-(1-methyl-1-(pyridin-2-yl)ethyl...
Scheme 11: Acetoxylation of compounds containing picolinamide and quinoline-8-amine moieties using the Pd(OAc)2...
Scheme 12: (CuOH)2CO3 catalyzed oxidative ortho-etherification using air as oxidant.
Scheme 13: Copper-catalyzed aerobic alkoxylation and aryloxylation of arenes containing pyridine-N-oxide moiet...
Scheme 14: Cobalt-catalyzed aerobic alkoxylation of arenes and alkenes containing pyridine N-oxide moiety.
Scheme 15: Non-symmetric double-fold C–H ortho-acyloxylation.
Scheme 16: N-nitroso directed ortho-alkoxylation of arenes.
Scheme 17: Selective alkoxylation and acetoxylation of alkyl groups.
Scheme 18: Acetoxylation of 2-alkylpyridines and related compounds.
Scheme 19: Acyloxylation and alkoxylation of alkyl fragments of substrates containing amide or sulfoximine dir...
Scheme 20: Palladium-catalyzed double sp3 C–H alkoxylation of N-(quinolin-8-yl)amides for the synthesis of sym...
Scheme 21: Copper-catalyzed acyloxylation of methyl groups of N-(quinolin-8-yl)amides.
Scheme 22: One-pot acylation and sp3 C–H acetoxylation of oximes.
Scheme 23: Possible mechanism of oxidative esterification catalyzed by N-heterocyclic nucleophilic carbene.
Scheme 24: Oxidative esterification employing stoichiometric amounts of aldehydes and alcohols.
Scheme 25: Selective oxidative coupling of aldehydes with alcohols in the presence of amines.
Scheme 26: Iodine mediated oxidative esterification.
Scheme 27: Oxidative C–O coupling of benzyl alcohols with methylarenes under the action of Bu4NI/t-BuOOH syste...
Scheme 28: Oxidative coupling of methyl- and ethylarenes with aromatic aldehydes under the action of Bu4NI/t-B...
Scheme 29: Cross-dehydrogenative C–O coupling of aldehydes with t-BuOOH in the presence of Bu4NI.
Scheme 30: Bu4NI-catalyzed α-acyloxylation reaction of ethers and ketones with aldehydes and t-BuOOH.
Scheme 31: Oxidative coupling of aldehydes with N-hydroxyimides and hexafluoroisopropanol.
Scheme 32: Oxidative coupling of alcohols with N-hydroxyimides.
Scheme 33: Oxidative coupling of aldehydes and primary alcohols with N-hydroxyimides using (diacetoxyiodo)benz...
Scheme 34: Proposed mechanism of the oxidative coupling of aldehydes and N-hydroxysuccinimide under action of ...
Scheme 35: Oxidative coupling of aldehydes with pivalic acid (172).
Scheme 36: Oxidative C–O coupling of aldehydes with alkylarenes using the Cu(OAc)2/t-BuOOH system.
Scheme 37: Copper-catalyzed acyloxylation of C(sp3)-H bond adjacent to oxygen in ethers using benzyl alcohols.
Scheme 38: Oxidative C–O coupling of aromatic aldehydes with cycloalkanes.
Scheme 39: Ruthenium catalyzed cross-dehydrogenative coupling of primary and secondary alcohols.
Scheme 40: Cross-dehydrogenative C–O coupling reactions of β-dicarbonyl compounds with sulfonic acids, acetic ...
Scheme 41: Acyloxylation of ketones, aldehydes and β-dicarbonyl compounds using carboxylic acids and Bu4NI/t-B...
Scheme 42: Acyloxylation of ketones using Bu4NI/t-BuOOH system.
Scheme 43: Cross-dehydrogenative C–O coupling of β-dicarbonyl compounds and their heteroanalogues with N-hydro...
Scheme 44: Cross-dehydrogenative C–O coupling of β-dicarbonyl compounds and their heteroanalogues with t-BuOOH....
Scheme 45: Oxidative C–O coupling of 2,6-dialkylphenyl-β-keto esters and thioesters with tert-butyl hydroxycar...
Scheme 46: α’-Acyloxylation of α,β-unsaturated ketones using KMnO4.
Scheme 47: Possible mechanisms of the acetoxylation at the allylic position of alkenes by Pd(OAc)2.
Scheme 48: Products of the oxidation of terminal alkenes by Pd(II)/AcOH/oxidant system.
Scheme 49: Acyloxylation of terminal alkenes with carboxylic acids.
Scheme 50: Synthesis of linear E-allyl esters by cross-dehydrogenative coupling of terminal alkenes wih carbox...
Scheme 51: Pd(OAc)2-catalyzed acetoxylation of Z-vinyl(triethylsilanes).
Scheme 52: α’-Acetoxylation of α-acetoxyalkenes with copper(II) chloride in acetic acid.
Scheme 53: Oxidative acyloxylation at the allylic position of alkenes and at the benzylic position of alkylare...
Scheme 54: Copper-catalyzed alkoxylation of methylheterocyclic compounds using di-tert-butylperoxide as oxidan...
Scheme 55: Oxidative C–O coupling of methylarenes with β-dicarbonyl compounds or phenols.
Scheme 56: Copper-catalyzed esterification of methylbenzenes with cyclic ethers and cycloalkanes.
Scheme 57: Oxidative C–O coupling of carboxylic acids with toluene catalyzed by Pd(OAc)2.
Scheme 58: Oxidative acyloxylation at the allylic position of alkenes with carboxylic acids using the Bu4NI/t-...
Scheme 59: Cross-dehydrogenative C–O coupling of carboxylic acids with alkylarenes using the Bu4NI/t-BuOOH sys...
Scheme 60: Oxidative C–O cross-coupling of methylarenes with ethyl or isopropylarenes.
Scheme 61: Phosphorylation of benzyl C–H bonds using the Bu4NI/t-BuOOH oxidative system.
Scheme 62: Selective C–H acetoxylation of 2,3-disubstituted indoles.
Scheme 63: Acetoxylation of benzylic position of alkylarenes using DDQ as oxidant.
Scheme 64: C–H acyloxylation of diarylmethanes, 3-phenyl-2-propen-1-yl acetate and dimethoxyarene using DDQ.
Scheme 65: Cross-dehydrogenative C–O coupling of 1,3-diarylpropylenes and 1,3-diarylpropynes with alcohols.
Scheme 66: One-pot azidation and C–H acyloxylation of 3-chloro-1-arylpropynes.
Scheme 67: Cross-dehydrogenative C–O coupling of 1,3-diarylpropylenes, (E)-1-phenyl-2-isopropylethylene and is...
Scheme 68: Cross-dehydrogenative C–O coupling of alkylarenes and related compounds with N-hydroxyphthalimide.
Scheme 69: Acetoxylation at the benzylic position of alkylarenes mediated by N-hydroxyphthalimide.
Scheme 70: C–O coupling of methylarenes with aromatic carboxylic acids employing the NaBrO3/NaHSO3 system.
Scheme 71: tert-Butyl peroxidation of allyl, propargyl and benzyl ethers catalyzed by Fe(acac)3.
Scheme 72: Cross-dehydrogenative C–O coupling of ethers with carboxylic acids mediated by Bu4NI/t-BuOOH system....
Scheme 73: Oxidative acyloxylation of dimethylamides and dioxane with 2-aryl-2-oxoacetic acids accompanied by ...
Scheme 74: tert-Butyl peroxidation of N-benzylamides and N-allylbenzamide using the Bu4NI/t-BuOOH system.
Scheme 75: Cross-dehydrogenative C–O coupling of aromatic carboxylic acids with ethers using Fe(acac)3 as cata...
Scheme 76: Cross-dehydrogenative C–O coupling of cyclic ethers with 2-hydroxybenzaldehydes using iron carbonyl...
Scheme 77: Cross-dehydrogenative C–O coupling of ethers with β-dicarbonyl compounds and phenols using copper c...
Scheme 78: Cross-dehydrogenative C–O coupling of 2-hydroxybenzaldehyde with dioxane catalyzed by Cu2(BPDC)2(BP...
Scheme 79: Ruthenium chloride-catalyzed acyloxylation of β-lactams.
Scheme 80: Ruthenium-catalyzed tert-butyl peroxydation amides and acetoxylation of β-lactams.
Scheme 81: PhI(OAc)2-mediated α,β-diacetoxylation of tertiary amines.
Scheme 82: Electrochemical oxidative methoxylation of tertiary amines.
Scheme 83: Cross-dehydrogenative C–O coupling of ketene dithioacetals with carboxylic acids in the presence of...
Scheme 84: Cross-dehydrogenative C–O coupling of enamides with carboxylic acids using iodosobenzene as oxidant....
Scheme 85: Oxidative alkoxylation, acetoxylation, and tosyloxylation of acylanilides using PhI(O(O)CCF3)2 in t...
Scheme 86: Proposed mechanism of the oxidative C–O coupling of actetanilide with O-nucleophiles in the presenc...
Scheme 87: Three-component coupling of aldehydes, anilines and alcohols involving oxidative intermolecular C–O...
Scheme 88: Oxidative coupling of phenols with alcohols.
Scheme 89: 2-Acyloxylation of quinoline N-oxides with arylaldehydes in the presence of the CuOTf/t-BuOOH syste...
Scheme 90: Cross-dehydrogenative C–O coupling of azoles with primary alcohols.
Scheme 91: Oxidation of dipyrroles to dipyrrins and subsequent oxidative alkoxylation in the presence of Na3Co...
Scheme 92: Oxidative dehydrogenative carboxylation of alkanes and cycloalkanes to allylic esters.
Scheme 93: Pd-catalyzed acetoxylation of benzene.
Double N-arylation reaction of polyhalogenated 4,4’-bipyridines. Expedious synthesis of functionalized 2,7-diazacarbazoles
- Mohamed Abboud,
- Emmanuel Aubert and
- Victor Mamane
Beilstein J. Org. Chem. 2012, 8, 253–258, doi:10.3762/bjoc.8.26
- diffraction and show π–π stacking involving the diazacarbazole moieties and the phenyl rings of functionalized groups. Keywords: 4,4’-bipyridine; cross-coupling; crystal packing; diazacarbazole; X-ray diffraction; Introduction Only a few examples of the preparation of diazacarbazoles have been reported [1
Graphical Abstract
Scheme 1: Cross-coupling reactions of bipyridines 2.
Scheme 2: Ligand effect in the double N-arylation of 2a with 6a.
Figure 1: Unsuccessful substrates in the double N-arylation of 2a.
Scheme 3: Functionalization of diazacarbazole 2a.
Scheme 4: Functionalized diazacarbazoles 12a–c from bipyridine 2b.
Figure 2: (a) ORTEP views showing the π–π (dashed lines) and selected C–H···π (dotted-dashed line) interactio...
