- Hypervalent iodine in synthesis. 77. An efficient method for the synthesis of N-arylindoles by the copper-catalyzed N-arylation of indole with diaryliodonium salts
-
N-arylindoles were prepared in good yields by copper-catalyzed N-arylation of indole with diaryliodonium salts.
- Zhou, Tao,Chen, Zhen-Chu
-
-
Read Online
- Unique CuI-pyridine based ligands catalytic systems for N-arylation of indoles and other heterocycles
-
Two pyridine-based ligands (N-((pyridin-2-yl) methyl) pyridin-2-amine) L1 and (N-((pyridin-2-yl) methylene) pyridin-2-amine) L2 are explored in present work which are inexpensive, effective and environmentally benign in their properties. These have been utilized for C-N cross coupling reaction resulting in N-arylation. The N-arylation of indole, imidazole and triazole have been successfully carried out with different aryl and heteroaryl halides using these ligands.
- Taywade, Amol,Chavan, Snehal,Ulhe, Avinash,Berad, Baliram
-
-
Read Online
- New polymer-bound haloarene chromium dicarbonyl isocyanide complexes: A successful study validating their use in solid-phase chemistry
-
New fluorobenzene chromium dicarbonylisocyanide complexes have been synthesized and evaluated in terms of their 'in solution' reactivity towards some nucleophiles. For the first time the polymer-bound isocyanides have been found to be valuable ligands for anchoring haloareneCr(CO)3 complexes by means of their substitution for a CO group. The supported fluorobenzene complex reacted with nitrogen-nucleophiles. (C) 2000 Elsevier Science Ltd.
- Maiorana,Baldoli,Licandro,Casiraghi,De Magistris,Paio,Provera,Seneci
-
-
Read Online
- Ceria-supported copper nanoparticles: A highly efficient and recyclable catalyst for N-arylation of indole
-
CuCeO2 catalytic nanomaterials have been synthesized by impregnation of ceria by copper acetate, followed by reduction and calcination under nitrogen. The components of these nanomaterials were characterized by means of XRD, XPS, N2
- Amadine, Othmane,Maati, Houda,Abdelouhadi, Karima,Fihri, Aziz,El Kazzouli, Sa?d,Len, Christophe,El Bouari, Abdeslam,Solhy, Abderrahim
-
-
Read Online
- Hoveyda-Grubbs catalyst analogues bearing the derivatives of: N -phenylpyrrol in the carbene ligand-structure, stability, activity and unique ruthenium-phenyl interactions
-
We have synthesized a series of N-phenylpyrrole and N-phenylindole carbenes and used them as ruthenium-ligating moieties in the synthesis of Hoveyda-Grubbs catalyst derivatives. We show that most of these complexes are difficult to synthesize and unstable apart from the N-phenylpyrrole-2,6-diisopropylphenyl ruthenium complex and its perbrominated derivative. These two systems are almost completely inactive in ring-closing metathesis at room temperature and become active only at 80 °C. DFT, SAPT0 and DLPNO-CCSD(T) calculations suggest that the rarely occurring phenyl-ruthenium interactions are responsible for the very slow initiation of these precatalysts at low temperatures.
- Grudzień,Trzaskowski,Smoleń,Gajda,Wo?niak,Grela
-
-
Read Online
- PEG3400-Cu2O-Cs2CO3: an efficient and recyclable microwave-enhanced catalytic system for ligand-free Ullmann arylation of indole and benzimidazole
-
A mild, simple and efficient microwave-enhanced copper-catalyzed protocol for N-arylation using high molecular weight poly(ethylene glycol) (PEG3400) as a solvent is reported. Indole and benzimidazole have been N-arylated in the presence of cup
- Colacino, Evelina,Villebrun, Laurent,Martinez, Jean,Lamaty, Frédéric
-
-
Read Online
- Chemical synthesis, spectroscopic studies, chemical reactivity properties and bioactivity scores of an azepin-based molecule
-
Azepines derived molecules are of great interest because of their multi-drug like properties and thus advantageous in biomedical field. Herein, a novel route is described for the synthesis of an azepine-based molecule, 10,11-Dibromo-10,11-dihydro- 5H-dibenzo[b,f]azepine-5-carbonyl chloride (DACC) by using dibutyltin dilaurate (DBTDL) as catalyst. The structure of DACC was elucidated by using FT-IR, NMR, and mass spectroscopic techniques. Several density functionals were considered for the study of the molecular properties of the synthesized compound. The global and local reactivity descriptors were estimated by using Conceptual Density Functional Theory (CDFT). The active sites suitable for the nucleophilic and electrophilic attacks were selected by linking them with the Fukui indices, Parr functions and condensed Dual Descriptor Δf(r). Finally, the bioactivity scores for the studied molecule were predicted through different methodologies.
- Kollur, Shiva Prasad,Castro, Joaquín Ortega,Frau, Juan,Glossman-Mitnik, Daniel
-
-
Read Online
- Double Ligands Enabled Ruthenium Catalyzed ortho-C?H Arylation of Dialkyl Biarylphosphines: Straight and Economic Synthesis of Highly Steric and Electron-Rich Aryl-Substituted Buchwald-Type Phosphines
-
A double-ligands enabled ruthenium catalyzed C(sp2)?H arylation of dialkyl phosphines is described, which provides a straight access to aryl-substituted dialkyl phosphine ligands. The combination of 1,3-diketone and amino acid ligands is essential for this transformation. An important six-membered cycloruthenium intermediate was successfully isolated and characterized by X-ray diffraction. Mechanistic studies showed that the 1,3-diketone promoted the process of oxidative addition of cycloruthenium intermediate. Some of modified CyJohnPhos ligands exhibited highly catalytic activity in palladium catalyzed C?N bond formation. (Figure presented.).
- Wang, Liang-Neng,Tang, Pan-Ting,Li, Ming,Li, Jia-Wei,Liu, Yue-Jin,Zeng, Ming-Hua
-
-
Read Online
- Cu(i) based catalysts derived from bidentate ligands and studies on the effect of substituents for: N -arylation of benzimidazoles and indoles
-
A family of Cu(i) complexes [Cu(L1-4)(Cl)(PPh3)] (C1-C4) were synthesized from bidentate ligands L1-L4 (where L1 = (E)-2-(2-benzylidene-1-phenylhydrazinyl)pyridine, L2 = (E)-N,N-dimethyl-4-((2-phenyl-2-(pyridin-2-yl)hydrazono)methyl)aniline, L3 = (E)-2-(2
- Kumari, Sheela,Ratnam, Anand,Mawai, Kiran,Chaudhary, Virendra Kumar,Mohanty, Aurobinda,Ghosh, Kaushik
-
-
Read Online
- Electrospun copper oxide nanoparticles as an efficient heterogeneous catalyst for N-arylation of indole
-
The N-arylation of indoles with a variety of aryl bromides is reported using copper oxide nanoparticles as a heterogeneous catalyst. These copper oxide nanoparticles, which were produced in a novel, facile, and scalable fashion via an electrospinning tech
- Khalil, Abdullah,Fihri, Aziz,Jouiad, Mustapha,Hashaikeh, Raed
-
-
Read Online
- Aromatic nucleophilic substitution on haloarene chromium tricarbonyl complexes: Mild N-arylation on indoles
-
A series of N-arylindoles were obtained in good yields and under mild conditions by nucleophilic substitution reaction of the sodium salt of indole on various haloarene chromium tricarbonyl complexes.
- Maiorana, Stefano,Baldoli, Clara,Del Buttero, Paola,Di Ciolo, Michela,Papagni, Antonio
-
-
Read Online
- Ligand complex of copper (II) supported on superparamagnetic Fe3O4?SiO2 nanoparticles: an efficient and magnetically separable catalyst for N-arylation of nitrogen-containing heterocycles with aryl halides
-
In this study, we introduce the ligand complex of copper (II) supported on superparamagnetic Fe3O4?SiO2 nanoparticles as a highly intriguing magnetic catalyst in N-arylation of nitrogen heterocycles with aryl halides. The present methodology offers several advantages such as; low catalyst loading, the use of magnetically recoverable and reusable catalyst, high to excellent yields without using any external ligands or additives, short reaction times and simplicity of operation. Also, the magnetic catalyst could be easily separated from the final product by an external magnet and reused up to seven times without any significant loss of activity. Therefore, this separation strategy with negligible leaching makes Fe3O4?SiO2/ligand/Cu(II) an economical catalyst to perform this transformation.
- Zahmatkesh, Saeed,Esmaeilpour, Mohsen,Mollaiy Poli, Azade
-
-
Read Online
- SiO2-functionalized melamine-pyridine group–supported Cu(OAc)2 as an efficient heterogeneous and recyclable nanocatalyst for the N-arylation of amines through Ullmann coupling reactions
-
This study reports a convenient approach to prepare SiO2/CCPy/Cu(OAc)2 as a novel nanocatalyst, in which melamine-bearing pyridine groups have functionalized SiO2 and can act as a capping agent to stabilize Cu(II) species.
- Hemmati, Saba,Naderi, Akram,Ghadermazi, Mohammad,Veisi, Hojat
-
-
Read Online
- Pd immobilized on modified magnetic Fe3O4 nanoparticles: Magnetically recoverable and reusable Pd nanocatalyst for Suzuki-Miyaura coupling reactions and Ullmann-type N-arylation of indoles
-
The Pd supported on amidoxime (AO)-functionalized Fe3O4 (Fe3O4/AO/Pd) hybrid material was used as an effective and recyclable nanocatalyst in Suzuki-Miyaura coupling reactions. The catalyst was very effective for the Suzuki-Miyaura reaction of aryl halides (Ar–I, Ar–Br, Ar–Cl) with phenylboronic acid and conversion was excellent in most cases. The yields of the products were in the range from 7–98%. The catalyst showed good stability and could be recovered and reused for six reaction cycles without a significant loss in its catalytic activity. Also, a wide range of N-arylated indoles are selectively synthesized through intermolecular C(aryl)–N bond formation from the corresponding aryl iodides and indoles through Ullmann-type coupling reactions in the presence of the prepared catalyst. [Figure not available: see fulltext.]
- Ghorbani-Vaghei, Ramin,Hemmati, Saba,Hekmati, Malak
-
-
Read Online
- Synthesis and characterization of nano-cellulose immobilized phenanthroline-copper (I) complex as a recyclable and efficient catalyst for preparation of diaryl ethers, N-aryl amides and N-aryl heterocycles
-
Functionalized nanocellulose was prepared and employed for immobilization of phenanthroline-copper(I) complex to afford cellulose nanofibril grafted heterogeneous copper catalyst [CNF-phen-Cu(I)]. This nanocatalyst was well characterized using FT-IR, NMR, XRD, CHNS, AAS, TGA, EDX and SEM. The activities of the synthesized catalyst were examined in the synthesis of diaryl ethers via C-O cross-coupling of phenols and aryl iodides, as well as, the preparation of N-aryl amides and N-aryl heterocycles through C-N cross-coupling of amides and N-H heterocycle compounds with aryl halides. In this trend, various substrates containing electron-donating and electron-withdrawing groups were exploited to evaluate the generality of this catalytic protocol. Accordingly, the catalyst demonstrated remarkable catalytic efficiency for both C-N and C-O cross-coupling reactions, thereby resulting in good to excellent yields of the desired products. Furthermore, the recoverability experiments of the catalyst showed that it can be readily retrieved by simple filtration and successfully reused several times with negligible loss of its catalytic activity.
- Aghili, Nora,Hosseinzadeh, Rahman,Mavvaji, Mohammad
-
-
- Synthesis of Non-Terminal Alkenyl Ethers, Alkenyl Sulfides, and N-Vinylazoles from Arylaldehydes or Diarylketones, DMSO and O, S, N-Nucleophiles
-
A transition-metal-free protocol for the synthesis of non-terminal alkenyl ethers, alkenyl sulfides, and N-vinylazoles from arylaldehydes or diarylketones, DMSO and O, S, N-nucleophiles has been reported. In this protocol, 24 examples of non-terminal alkenyl ethers and 28 examples of non-terminal alkenyl sulfides in 72–95% yields have been synthesized within 5 min. Moreover, 27 examples of non-terminal N-vinylazoles with 57–88% yields have also been synthesized within 2 hours. The preliminary mechanism investigations revealed that arylaldehydes or diarylketones offered a carbon atom, DMSO provided a methine and O, S, N-nucleophiles contributed one X atom for constructing C=C?X structure. (Figure presented.).
- Nie, Zhiwen,Lv, Huifang,Yang, Tonglin,Su, Miaodong,Luo, Weiping,Liu, Qiang,Guo, Cancheng
-
supporting information
p. 1473 - 1480
(2022/04/03)
-
- Photocatalyst-Free, Visible-Light-Mediated C(sp3)-H Arylation of Amides via a Solvent-Caged EDA Complex
-
A photocatalyst-free and mild visible light photochemical procedure for C(sp3)-H arylation of amides is described. The reaction proceeds via an electron donor-acceptor (EDA) complex between an electron-rich arene substrate and electron-poor persulfate oxi
- Kaur, Jaspreet,Shahin, Ahmed,Barham, Joshua P.
-
supporting information
p. 2002 - 2006
(2021/03/08)
-
- Copper nanoparticle anchored biguanidine-modified Zr-UiO-66 MOFs: a competent heterogeneous and reusable nanocatalyst in Buchwald-Hartwig and Ullmann type coupling reactions
-
We have designed a functionalized metal-organic framework (MOF) of UiO topology as a support, with an extremely high surface area, adjustable pore sizes and stable crystalline coordination polymeric structure and implanted copper (Cu) nanoparticles thereon. The core three dimensional Zr-derived MOF (UiO-66-NH2) was modified with a biguanidine moiety following a covalent post-functionalization approach. The morphological and physicochemical features of the material were determined using analytical methods such as FT-IR, SEM, TEM, EDX, atomic mapping, XRD and ICP-OES. The SEM and XRD results justified the unaffected morphology of Zr-MOF after structural modifications. The as-synthesized UiO-66-biguanidine/Cu nanocomposite was catalytically explored in the aryl and heteroaryl Buchwald-Hartwig C-N and Ullmann type C-O cross coupling reactions with excellent yields. A library of biaryl amine and biaryl ethers was synthesized over the catalyst under mild and green conditions. Furthermore, the catalyst was isolated by centrifugation and recycled 11 times with no significant copper leaching or change in its activity.
- Veisi, Hojat,Neyestani, Narges,Pirhayati, Mozhgan,Ahany Kamangar, Sheida,Lotfi, Shahram,Tamoradi, Taiebeh,Karmakar, Bikash
-
p. 22278 - 22286
(2021/07/02)
-
- Functionalization of superparamagnetic Fe3O4@SiO2 nanoparticles with a Cu(II) binuclear Schiff base complex as an efficient and reusable nanomagnetic catalyst for N-arylation of α-amino acids and nitrogen-containing heterocycles with aryl halides
-
Fe3O4@SiO2 nanoparticles was functionalized with a binuclear Schiff base Cu(II)-complex (Fe3O4@SiO2/Schiff base-Cu(II) NPs) and used as an effective magnetic hetereogeneous nanocatalyst for the N-arylation of α-amino acids and nitrogen-containig heterocycles. The catalyst, Fe3O4@SiO2/Schiff base-Cu(II) NPs, was characterized by Fourier transform infrared (FTIR) and ultraviolet-visible (UV-vis) analyses step by step. Size, morphology, and size distribution of the nanocatalyst were studied by transmission electron microscopy (TEM), scanning electron microscopy (SEM), and dynamic light scatterings (DLS) analyses, respectively. The structure of Fe3O4 nanoparticles was checked by X-ray diffraction (XRD) technique. Furthermore, the magnetic properties of the nanocatalyst were investigated by vibrating sample magnetometer (VSM) analysis. Loading content as well as leaching amounts of copper supported by the catalyst was measured by inductive coupled plasma (ICP) analysis. Also, thermal studies of the nanocatalyst was studied by thermal gravimetric analysis (TGA) instrument. X-ray photoelectron spectroscopy (XPS) analysis of the catalyst revealed that the copper sites are in +2 oxidation state. The Fe3O4@SiO2/Schiff base-Cu(II) complex was found to be an effective catalyst for C–N cross-coupling reactions, which high to excellent yields were achieved for α-amino acids as well as N-hetereocyclic compounds. Easy recoverability of the catalyst by an external magnet, reusability up to eight runs without significant loss of activity, and its well stability during the reaction are among the other highlights of this catalyst.
- Sardarian,Kazemnejadi,Esmaeilpour
-
-
- An organic compound and an organic light emitting diode
-
The present invention relates to a novel organic compound and an organic light emitting device comprising the same. More particularly, the present invention relates to an organic compound having excellent lifetime, efficiency, electrochemical stability, a
- -
-
Paragraph 0293-0297
(2021/07/17)
-
- Manganese(III) Acetate Catalyzed Aerobic Dehydrogenation of Tertiary Indolines, Tetrahydroquinolines and an N-Unsubstituted Indoline
-
A Mn(OAc)3 ? 2H2O-catalyzed aerobic dehydrogenation of five and six-membered N-heterocycles for the synthesis of N-heteroarenes is reported. Of note, this protocol can be applied to the dehydrogenation of tertiary indolines with various electron-deficient N-substituents. Preliminary mechanistic investigations support that a single-electron transfer pathway might be involved. (Figure presented.).
- Niu, Xiaokang,Yang, Lei
-
supporting information
p. 4209 - 4215
(2021/08/06)
-
- Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations
-
Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.
- Liu, Shuyang,Tian, Miao,Bu, Xiubin,Tian, Hua,Yang, Xiaobo
-
supporting information
p. 7738 - 7744
(2021/05/07)
-
- Preparation method of N-arylindole under copper catalysis
-
The invention provides a preparation method of N-arylindole under copper catalysis. The preparation method comprises the following steps: S1, selecting a proper amount of a reaction reagent, a catalyst, a solvent and the like; S2, sequentially adding the
- -
-
Paragraph 0063; 0097-0104
(2021/07/08)
-
- Ni-catalyzed reductive decyanation of nitriles with ethanol as the reductant
-
A nickel-catalyzed reductive decyanation of aromatic nitriles has been developed, in which the readily available and abundant ethanol was applied as the hydride donor. Various functional groups on the aromatic rings, such as alkoxyl, amino, imino and amide, were compatible in this catalytic protocol. Heteroaryl, benzylic and alkenyl nitriles were also tolerated. Mechanistic investigation indicated that ethanol provided hydride efficientlyviaβ-hydride elimination in this reductive decyanation.
- Wu, Ke,Ling, Yichen,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu,Jin, Liqun,Hu, Xinquan
-
supporting information
p. 2273 - 2276
(2021/03/09)
-
- A Pd/Cu-Free magnetic cobalt catalyst for C-N cross coupling reactions: synthesis of abemaciclib and fedratinib
-
Herein, the synthesis of a nano-catalytic system comprising magnetic nanoparticles as the core and edible natural ligands bearing functional groups as supports for cobalt species is described. Subsequent to its characterization, the efficiency of the catalyst was investigated for C-N cross-coupling reactions using assorted derivatives of amines and aryl halides. This novel and easily accessible Pd- and Cu-free catalyst exhibited good catalytic activity in these reactions using γ-valerolactone (GVL) at room temperature; good recyclability bodes well for the future application of this strategy. The introduced catalytic system is attractive in view of the excellent efficiency in an array of coupling reactions and its versatility is illustrated in the synthesis of abemaciclib and fedratinib, which are FDA-approved new and significant anti-cancer medicinal compounds that are prepared under green reaction conditions.
- Hajipour, Abdol R.,Khorsandi, Zahra,Sarfjoo, Mohamad Reza,Varma, Rajender S.
-
supporting information
p. 5222 - 5229
(2021/07/29)
-
- A ligand-free copper-catalyzed strategy to the N-arylation of indazole using aryl bromides
-
A simple and efficient strategy for the C–N cross-coupling of indazole with a variety of substituted aryl bromides is reported. Under the optimized conditions, a broad scope of N-arylated products were obtained in good to excellent yields (up to 87%) under the ligand-free conditions.
- Bai, Di-Xiang,Lim, Rachel Sin-Ee,Ng, Hui-Fen,Teo, Yong-Chua
-
supporting information
p. 1398 - 1405
(2021/03/08)
-
- Scope, Kinetics, and Mechanism of “On Water” Cu Catalysis in the C–N Cross-Coupling Reactions of Indole Derivatives
-
A simple and cost-effective protocol for the C–N cross coupling of indole derivatives with aryl iodides using CuI/phenanthroline catalytic system in aqueous and DME/H2O solvent mixture is described. The reactions were performed in the absence of phase-transfer catalyst, and afforded N-arylated products in moderate to excellent yields under mild reaction conditions. A systematic tuning of reaction conditions using DME as a co-solvent enables to improve product yields of N-arylation reactions. The broad substrate scope, easy performance, and low loading of catalyst as well as ligand render this approach appropriate for large scale processes. The mechanism of “on water” Cu-catalyzed N-arylation reaction is investigated using kinetic and computational studies, which reveal interesting mechanistic aspects of the reaction. A series of kinetic experiments showed significant rate enhancement for “on water” Cu-catalyzed N-arylation over the reaction performed in the organic solvent (DME). Computational studies corroborated “on water” rate acceleration by delineating the role of water in the reaction. The water induces rate acceleration by stabilizing the transition state of oxidative addition through hydrogen bonding interactions, presumably at the oil-water interface, and thus helps to reduce the free energy of activation of oxidative addition of iodobenzene to the Cu complex, which is identified as the rate-limiting step of reaction.
- Malavade, Vrunda,Patil, Manish,Patil, Mahendra
-
supporting information
p. 561 - 569
(2020/02/05)
-
- Cu(I)-anchored polyvinyl alcohol coated-magnetic nanoparticles as heterogeneous nanocatalyst in Ullmann-type C–N coupling reactions
-
In this paper, the preparation of a novel magnetic nanocatalyst (Fe3O4?PVA/CuCl) is described, which involves coating of polyvinyl alcohol (PVA) onto the surface of Fe3O4 nanoparticles and its subsequent coordination with CuCl catalyst. The nanocatalyst was characterized by various analytical methods, including Fourier-transform infrared, X-ray diffraction, inductively coupled plasma spectroscopy, field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy (EDX), transmission electron microscopy, vibrating-sample magnetometry, and EDX elemental mapping. Moreover, the nanocatalyst was efficiently used in the N-arylation of amines via the formation of a carbon–nitrogen bond between the aryl halides and amines by Ullmann-type coupling reactions. The catalyst was sufficiently stable and can be reused for at least seven times in a model Ullmann reaction without remarkable alteration in its catalytic behavior. Heterogeneity of the catalyst was investigated by a hot filtration test.
- Ahany Kamangar, Sheida,Hashemi Salehi, Mirmehdi,Hekmati, Malak,Hemmati, Saba,Yousefi, Mohammad
-
-
- A Co-Cu bimetallic magnetic nanocatalyst with synergistic and bifunctional performance for the base-free Suzuki, Sonogashira, and C-N cross-coupling reactions in water
-
A novel magnetically recyclable bimetallic catalyst was prepared by anchoring imidazolium moiety and PEG chains on Fe3O4 NPs and named as Fe3O4?PEG/Cu-Co. It was found to be a powerful catalyst for the Sonogashira, Suzuki, and C-N cross-coupling reactions in water as a green solvent without the need for any external base. Fe3O4?PEG/Cu-Co was well characterized with FT-IR, FE-SEM, TEM, VSM, EDX, ICP, UV-visible, CV, and XPS analyses. Optimum ranges of parameters such as time, temperature, and amount of catalyst were investigated by Design-Expert 10.0.7 software for C-C Suzuki, Sonogashira, and C-N cross-coupling reactions to find the optimum conditions. The catalyst was compatible with a variety of aryl halides and N-arenes and gave favorable coupling products with good to high yields for all of them. Hot filtration and Hg poisoning tests involving the nanocatalyst revealed the stability, low metal leaching, and heterogeneous nature of the catalyst. Reaction mechanisms were proposed by study of the UV-visible spectra in situ as well as hydroquinone tests during the progress of reactions. In situ XPS analysis was also used to study the reaction mechanism. To prove the synergistic performance of Co and Cu in the catalyst, its various homologues were synthesized and applied to a model reaction separately, and then their catalytic activities were investigated. Finally, the catalyst could be recovered from the reaction mixture simply, and reused for several cycles with a minimum loss in catalytic activity and performance.
- Allahresani, Ali,Kazemnejadi, Milad,Nasseri, Mohammad Ali,Rezazadeh, Zinat
-
p. 10645 - 10660
(2020/09/18)
-
- Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine
-
The polystyrene-cross-linking bisphosphine ligand PS-DPPBz was effective for the Ir-catalyzed reversible acceptorless dehydrogenation/hydrogenation of N-heterocycles. Notably, this protocol is applicable to the dehydrogenation of N-substituted indoline derivatives with various N-substituents with different electronic and steric natures. A reaction pathway involving oxidative addition of an N-adjacent C(sp3)-H bond to a bisphosphine-coordinated Ir(I) center is proposed for the dehydrogenation of N-substituted substrates.
- Zhang, Deliang,Iwai, Tomohiro,Sawamura, Masaya
-
supporting information
p. 5240 - 5245
(2020/07/03)
-
- Catalytic Aerobic Dehydrogenatin of N-Heterocycles by N-Hydoxyphthalimide
-
Catalytic methods for the aerobic dehydrogenation of N-heterocycles are reported. In most cases, indoles are accessed efficiently from indolines using catalytic N-hydroxyphthalimide (NHPI) as the sole additive under air. Further studies revealed an improved catalytic system of NHPI and copper for the preparation of other heteroaromatics, for example quinolines. (Figure presented.).
- Chen, Weidong,Tang, Hao,Wang, Weilin,Fu, Qiang,Luo, Junfei
-
supporting information
p. 3905 - 3911
(2020/08/10)
-
- Method for preparing indole compound through air oxidation catalyzed by N-hydroxyphthalimide
-
The invention discloses a method for preparing an indole compound through non-transition metal catalyzed air oxidation. According to the method, the low-cost N-hydroxyphthalimide is used as a catalystand air is used as an oxidizing agent, wherein indoline compounds are oxidized in an organic solvent, and synthesis of the indoline compounds is achieved. The method has the advantages of simple reaction operation, low reaction cost, high yield, mild conditions, no heavy metal pollution and the like.
- -
-
Paragraph 0095-0097
(2020/11/23)
-
- N -Arylation of (hetero)arylamines using aryl sulfamates and carbamates via C-O bond activation enabled by a reusable and durable nickel(0) catalyst
-
An effective and general aryl amination protocol has been developed using a magnetically recoverable Ni(0) based nanocatalyst. This new stable catalyst was prepared on Fe3O4@SiO2 modified by EDTA and investigated by FT-IR, EDX, TEM, XRD, DLS, FE-SEM, XPS, NMR, TGA, VSM, ICP and elemental analysis techniques. The reaction proceeded via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles with good to excellent yields. Furthermore, the catalyst could be easily recovered by using an external magnetic field and directly reused at least six times without notable reduction in its activity. This journal is
- Dindarloo Inaloo, Iman,Majnooni, Sahar,Eslahi, Hassan,Esmaeilpour, Mohsen
-
p. 13266 - 13278
(2020/10/07)
-
- Structure Ligation Relationship of Amino Acids for the Selective Indole C?H Arylation Reaction: L-Aspartic acid as Sustainable Alternative of Phosphine Ligands
-
The Structure Ligation Relationship (SLR) of free amino acids (AAs) under Pd-catalysis were examined for the chemo- and regio-selective indole C?H arylation reactions. While the majority of AAs were minor or ineffective, the L-aspartic acid (L-Asp) stands out promising to deliver high-value C3-arylated indoles with excellent chemo- (C vs N) and regioselectivity (C3 vs C2) with high functional group tolerance. Thus, the protocol offers a cost-effective and sustainable alternative of phosphine-based ligands for the indole C3?H arylation reactions. Preliminary mechanistic investigations suggested the simultaneous involvement of ?NH2, α-CO2H, and β-CO2H functionalities of L-Asp and found critical for its ligation efficiency. The developed catalytic system was compatible with the tandem decarboxylation/arylation procedure for the chemoselective synthesis of 3-aryl indoles. (Figure presented.).
- Lokhande?, Shyam Kumar,Vaidya?, Gargi Nikhil,Satpute, Dinesh Parshuram,Venkatesh, Ashwini,Kumar, Sanjeev,Kumar, Dinesh
-
p. 2857 - 2863
(2020/06/09)
-
- Nickel-Catalyzed Decarbonylative Amination of Carboxylic Acid Esters
-
The reaction of carboxylic acid derivatives with amines to form amide bonds has been the most widely used transformation in organic synthesis over the past century. Its utility is driven by the broad availability of the starting materials as well as the kinetic and thermodynamic driving force for amide bond formation. As such, the invention of new reactions between carboxylic acid derivatives and amines that strategically deviate from amide bond formation remains both a challenge and an opportunity for synthetic chemists. This report describes the development of a nickel-catalyzed decarbonylative reaction that couples (hetero)aromatic esters with a broad scope of amines to form (hetero)aryl amine products. The successful realization of this transformation was predicated on strategic design of the cross-coupling partners (phenol esters and silyl amines) to preclude conventional reactivity that forms inert amide byproducts.
- Malapit, Christian A.,Borrell, Margarida,Milbauer, Michael W.,Brigham, Conor E.,Sanford, Melanie S.
-
supporting information
p. 5918 - 5923
(2020/04/08)
-
- Hydrogen-Transfer-Mediated N-Arylation of Naphthols Using Indolines as Hydrogen Donors
-
Using a hydrogen-transfer-mediated activation mode, we report a new catalytic system for the transfer hydrogenation of naphthols. In the presence of the Pd/C catalyst and base, various naphthols reacted with indolines to afford N-aryl-substituted heterocyclic compounds. Indolines were found to act as novel hydrogen donors for naphthols under palladium catalysis. This method features good functional tolerance, operational simplicity, and a readily available catalyst.
- Chen, Xiuwen,Yang, Zhihai,Chen, Xuyan,Liang, Wanyi,Zhu, Zhongzhi,Xie, Feng,Li, Yibiao
-
p. 508 - 514
(2020/01/11)
-
- New Insights into the Reaction Capabilities of Ionic Organic Bases in Cu-Catalyzed Amination
-
The application of ionic organic bases in the copper-catalyzed amination reaction (Ullmann reaction) has been studied at room temperature, with sub-mol-% catalyst loadings, and with more challenging amines at elevated temperatures. The cation present in the base has been shown to have little effect on the reaction at standard catalyst and ancillary ligand loadings, whereas the choice of anion is crucial for good reactivity. A substrate scope carried out at room temperature with the best performing bases, TBAM and TBPM, showed both bases to be highly effective under these mild reaction conditions. Moreover, under sub-mol % catalyst loadings and room temperature conditions, TBPM gave good to excellent yields for a number of different amines and functionalized aryl iodides (14 examples). However, reactions involving more challenging amines gave little or no yield. By using more forceful conditions (120 °C) moderate to excellent yields of cross-coupled products containing more challenging amines was achievable using TBPM and to a lesser extent with TBAM. As part of this work a study on the stability of the organic bases at 120 °C was undertaken. TBAM is shown to decompose to give nBu3N and mono-butylmalonate at higher temperatures, and this can be correlated to a decrease in performance in the coupling reaction. The phosphonium cations in TBPM did not undergo analogous reactivity but were shown instead to experience some degree of deprotonation at the α-CH2 to generate phosphonium ylides. This however did not lead to a significantly degradation in the activity of the TBPM in the cross-coupling reaction.
- Lo, Quintin A.,Sale, David,Braddock, D. Christopher,Davies, Robert P.
-
p. 1944 - 1951
(2019/02/19)
-
- CuCl2 heterogenized on metformine-modified polystyrene resin as an antibacterial agent and recyclable nanocatalyst for Ullmann-type C-N coupling reactions
-
Merrifield Resin was functionalized with metformine and applied as a solid support to immobilize the CuCl2. The Ps-Met/CuCl2 was characterized by several techniques including Fourier transform infrared (FTIR), field emission scanning electron microscopy (FESEM), energy-dispersive X-ray spectroscopy (EDX), wavelength-dispersive X-ray spectroscopy (WDX) and inductively coupled plasma (ICP). The Ps-Met/CuCl2 was used as an efficient recyclable solid nanocatalyst for N-arylation of indole and aniline through coupling reactions of Ullmann-type C-N. The advantages of this method are easy workup, improved yields, and simple recovery via filtration. Ultimately, the Ps-Met/CuCl2 antibacterial property was examined against two bacteria (Staphylococcus aureus (Staph. aureus) and Escherichia coli (E. coli)) and indicated its antibacterial performance against gram negative (E. coli) bacteria and gram positive (Staph. aureus).
- Veisi, Hojat,Ahmadian, Hossein,Mirshokraie, Seyed Ahmad,Didehban, Khadijeh,Zangeneh, Mohammad Mahdi
-
-
- Structure Ligation Relationship of Amino Acids for the Amination Cross-Coupling Reactions
-
The structure ligation relationship (SLR) of amino acids (AAs) for the cross-coupling aminations was examined. While AA ligated C-N cross-couplings under Pd and Ni catalysis were minor or ineffective, the AA ligated Cu-catalyzed C-N cross-couplings were promising particularly with the use of l-methionine. The roles of -NH2, -CO2H, and -S- of l-methionine were investigated and found critical for their ligation efficiency. The finding was compatible with aromatic as well as aliphatic amines including tautomerizable N-heteroarenes.
- Vaidya, Gargi Nikhil,Khan, Arif,Verma, Hansa,Kumar, Sanjeev,Kumar, Dinesh
-
supporting information
p. 3004 - 3010
(2019/03/07)
-
- Indoloindole as a new building block of a hole transport type host for stable operation in phosphorescent organic light-emitting diodes
-
An organic material for application as a p-type host of phosphorescent organic light-emitting diodes was newly developed using an indoloindole moiety as a hole transport unit. The indoloindole derived organic material showed better hole transport properti
- Lee, Ha Lim,Lee, Kyung Hyung,Lee, Jun Yeob
-
p. 5988 - 5994
(2019/06/03)
-
- Electrochemical Regioselective Bromination of Electron-Rich Aromatic Rings Using n Bu 4 NBr
-
Electrochemical regioselective bromination of electron-rich aromatic rings using stoichiometric tetrabutylammonium bromide (n Bu 4 NBr) has been accomplished under mild conditions. This protocol provides an environmentally friendly and simple way for the construction of C-Br bond in moderate to high yields with wide functional group tolerance.
- Bai, Ya,Che, Xin,Liu, Nian,Ning, Shulin,Shi, Lingling,Wang, Shutao,Wang, Siyu,Xiang, Jinbao,Xie, Wenxia
-
supporting information
p. 1313 - 1316
(2019/06/20)
-
- Copper-Catalyzed NaBAr 4-Based N-Arylation of Amines
-
Using NaBAr 4 as an arylating agent, the formation of carbon-heteroatom bonds by a Cham-Lam cross-coupling reaction in the presence of catalytic copper(II) acetate monohydrate in acetonitrile at room temperature under air is described. The investigation of reaction scope suggests that several aliphatic and aromatic amines are compatible. In particular, the reaction of alkylamine and NaBAr 4 proceeds smoothly to offer the corresponding products in good to excellent yields.
- Yang, Qin,Lei, Xiaoli,Yin, Zhijian,Deng, Zhihong,Peng, Yiyuan
-
supporting information
p. 538 - 544
(2019/01/10)
-
- Iron oxide encapsulated by copper-Apatite: An efficient magnetic nanocatalyst for: N-Arylation of imidazole with boronic acid
-
N-Arylation of imidazole was carried out with various arylboronic acids on iron oxide encapsulated by copper-Apatite (Fe3O4?Cu-Apatite), producing excellent yields. Firstly, the iron nanoparticles were prepared using a solvothermal m
- Amadine, Othmane,Essamlali, Younes,Amedlous, Abdallah,Zahouily, Mohamed
-
p. 36471 - 36478
(2019/11/20)
-
- Nickel-catalyzed N-arylation of amines with arylboronic acids under open air
-
In this study, a well-defined, novel NHC-Ni complex was developed and used to catalyze the N-arylation of alkyl- and arylamines with arylboronic acids in a rare version of Chan-Lam coupling. Although the same coupling using copper catalysts has been widely studied, the nickel-catalyzed version is rare and normally requires 10–20 mol% catalyst loading. This novel NHC-Ni complex in combination with 4,4′-dimethyl-2,2′-bipyridine, however, proved to be an effective catalyst that lowered the required catalyst loading to only 2.0 mol%.
- Ando, Shin,Hirota, Yurina,Matsunaga, Hirofumi,Ishizuka, Tadao
-
supporting information
p. 1277 - 1280
(2019/04/10)
-
- Replacement of Stoichiometric DDQ with a Low Potential o-Quinone Catalyst Enabling Aerobic Dehydrogenation of Tertiary Indolines in Pharmaceutical Intermediates
-
A transition-metal/quinone complex, [Ru(phd)3]2+ (phd = 1,10-phenanthroline-5,6-dione), is shown to be effective for aerobic dehydrogenation of 3° indolines to the corresponding indoles. The results show how low potential quinones may be tailored to provide a catalytic alternative to stoichiometric DDQ, due to their ability to mediate efficient substrate dehydrogenation while also being compatible with facile reoxidation by O2. The utility of the method is demonstrated in the synthesis of key intermediates to pharmaceutically important molecules.
- Li, Bao,Wendlandt, Alison E.,Stahl, Shannon S.
-
supporting information
p. 1176 - 1181
(2019/02/14)
-
- Base-promoted SNAR reactions of fluoro- And chloroarenes as a route to N-aryl indoles and carbazoles
-
KOH/DMSO-promoted C-N bond formation via nucleophilic aromatic substitution (SNAr) between chloroarenes or fluoroarenes with indoles and carbazole under transition metal-free conditions affording the corresponding N-arylated indoles and carbazoles has been developed.
- Iqbal, Muhammad Asif,Mehmood, Hina,Lv, Jiaying,Hua, Ruimao
-
-
- Palladium-Catalyzed C-N Cross-Coupling of NH-Heteroarenes and Quaternary Ammonium Salts via C-N Bond Cleavage
-
In this paper, we extend the substrate class of Buchwald-Hartwig amination to quaternary ammonium salts. In the presence of Pd(OAc)2 and t-BuXPhos, the coupling of aryl- or arylmethyltrimethylammonium triflates with NH-heteroarenes via C-N bond cleavage affords the desired N-aryl or N-arylmethyl heteroarenes in moderate to excellent yields.
- Chen, Hongyi,Yang, Hongqin,Li, Nutao,Xue, Xinghua,He, Ze,Zeng, Qingle
-
p. 1679 - 1685
(2019/08/20)
-
- Nickel-catalyzed decarbonylation of: N -acylated N-heteroarenes
-
Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes is developed. This method can be used to produce a variety of N-aryl heteroarenes, including pyrroles, indoles, carbazoles and phenoxazines, using benzoic acid derivatives as arylating reagents. Arylnickelamide intermediates that are relevant to the catalytic reaction were characterized by X-ray crystallography. When N-acylated benzimidazoles are used as substrates, decarbonylation accompanied 1,2-migration to form 2-arylated benzimidazoles.
- Morioka, Toshifumi,Nakatani, Syun,Sakamoto, Yuki,Kodama, Takuya,Ogoshi, Sensuke,Chatani, Naoto,Tobisu, Mamoru
-
p. 6666 - 6671
(2019/07/17)
-
- Palladium-catalyzed c(sp2)-n bond cross-coupling with triaryl phosphates
-
The first general palladium-catalyzed amination of aryl phosphates is described. The combination of MorDalPhos with [Pd(-cinnamyl)Cl]2 enables the amination of electron-rich, electron-neutral, and electron-poor aryl phosphates with a board range of aromatic, aliphatic, and heterocyclic amines. Common functional groups such as ether, keto, ester, and nitrile show an excellent compatibility in this reaction condition. The solvent-free amination reactions are also successful in both solid coupling partners. The gram-scale cross-coupling is achieved by this catalytic system.
- Chen, Zicong,Chen, Xiangmeng,So, Chau Ming
-
-
- Palladium-Catalyzed C(sp2)-N Bond Cross-Coupling with Triaryl Phosphates
-
The first general palladium-catalyzed amination of aryl phosphates is described. The combination of MorDalPhos with [Pd(?-cinnamyl)Cl]2 enables the amination of electron-rich, electron-neutral, and electron-poor aryl phosphates with a board range of aromatic, aliphatic, and heterocyclic amines. Common functional groups such as ether, keto, ester, and nitrile show an excellent compatibility in this reaction condition. The solvent-free amination reactions are also successful in both solid coupling partners. The gram-scale cross-coupling is achieved by this catalytic system.
- Chen, Zicong,Chen, Xiangmeng,So, Chau Ming
-
p. 6366 - 6376
(2019/05/24)
-
- Copper-Catalyzed Decarboxylative N -Arylation of Indole-2-carboxylic Acids
-
A novel decarboxylative N -arylation of indole-2-carboxylic acids with aryl halides is developed. The reaction proceeds efficiently in the presence of Cu 2 O as the catalyst to give the corresponding N -aryl indoles in high yields. This synthet
- Zhang, Yan,Hu, Zhe-Yao,Li, Xin-Chang,Guo, Xun-Xiang
-
p. 1803 - 1808
(2019/04/05)
-
- Recyclable bimetallic CuMoO4 nanoparticles for C-N cross-coupling reaction under mild conditions
-
Herein we disclosed inexpensive copper(ii) bimetallic CuMoO4 nanoparticles for the C-N cross-coupling reaction of alkyl and aryl amines with haloarenes. The reaction proceeds under mild and ligand free conditions. The catalyst is recyclable and effective for a wide range of amines and haloarenes. Here, the efficiency of the Cu(ii) catalyst is increased by doping molybdenum metal. The bimetallic nanoparticles are anticipated to proceed via normal oxidative addition and reductive eliminations.
- Panigrahi, Reba,Panda, Subhalaxmi,Behera, Pradyota Kumar,Sahu, Santosh Kumar,Rout, Laxmidhar
-
supporting information
p. 19274 - 19278
(2019/12/24)
-
- Tryptamine Synthesis by Iron Porphyrin Catalyzed C?H Functionalization of Indoles with Diazoacetonitrile
-
The functionalization of C?H bonds with non-precious metal catalysts is an important research area for the development of efficient and sustainable processes. Herein, we describe the development of iron porphyrin catalyzed reactions of diazoacetonitrile with N-heterocycles yielding important precursors of tryptamines, along with experimental mechanistic studies and proof-of-concept studies of an enzymatic process with YfeX enzyme. By using readily available FeTPPCl, we achieved the highly efficient C?H functionalization of indole and indazole heterocycles. These transformations feature mild reaction conditions, excellent yields with broad functional group tolerance, can be conducted on gram scale, and thus provide a unique streamlined access to tryptamines.
- Hock, Katharina J.,Knorrscheidt, Anja,Hommelsheim, Renè,Ho, Junming,Weissenborn, Martin J.,Koenigs, Rene M.
-
supporting information
p. 3630 - 3634
(2019/02/13)
-
- CuCl heterogenized on metformine-modified multi walled carbon nanotubes as a recyclable nanocatalyst for Ullmann-type C-O and C-N coupling reactions
-
Herein, a novel MWCNTs-Met/CuCl nanocatalyst synthesis method by metformine covalent grafting on the surface of carbon nanotubes and subsequent coordination with a CuCl catalyst is described. The nanocatalyst formation was analyzed by FTIR, energy dispersive spectroscopy (EDS), Raman spectroscopy and ICP analysis. The nanocatalyst morphology was examined by transmission and scanning electron microscopies (TEM and SEM). Moreover, in the N-arylation of anilines and indole, the nanocatalyst (MWCNTs-Met/CuCl) could be successfully used by formation of intermolecular C(aryl)-N bonds of the relevant aryl halides (Ar-I, Ar-Br, Ar-Cl) with amines by coupling reactions of Ullmann-type. The O-arylation of substituted phenols is also promoted by this heterogeneous copper catalyst with different aryl iodides and bromides. Additionally, without any considerable loss in activity, the novel catalyst was recovered and recycled several times.
- Akhavan, Elham,Hemmati, Saba,Hekmati, Malak,Veisi, Hojat
-
p. 2782 - 2789
(2018/02/19)
-
- Copper(I)-USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type O-, N-, S-, and C-Arylation Reactions: Scope and Application to Total Synthesis
-
The copper(I)-doped zeolite CuI-USY proved to be a versatile, efficient, and recyclable catalyst for various Ullmann-type coupling reactions. Easy to prepare and cheap, this catalytic material enables the arylation and heteroarylation of diverse O-, N-, S-, and C-nucleophiles under ligand-free conditions while exhibiting large functional group compatibility. The facility of this catalyst to promote C-O bond formation was further demonstrated with the total synthesis of 3-methylobovatol, a naturally occurring diaryl ether of biological relevance. From a mechanistic viewpoint, two competitive pathways depending on the nature of the nucleophile and consistent with the obtained results have been proposed.
- Garnier, Tony,Danel, Mathieu,Magné, Valentin,Pujol, Anthony,Bénéteau, Valérie,Pale, Patrick,Chassaing, Stefan
-
p. 6408 - 6422
(2018/05/31)
-
- Palladium(II) anchored on polydopamine coated-magnetic nanoparticles (Fe3O4&at;PDA&at;Pd(II)): A heterogeneous and core–shell nanocatalyst in Buchwald–Hartwig C–N cross coupling reactions
-
An efficient method was proposed to synthesize polydopamine (PDA)-coated Fe3O4 nanoparticles (Fe3O4&at;PDA). For the first time, effective deposition of Pd complex is explained by using Fe3O4&at;PDA as a core–shell magnetic coordinator and stabilizer agent. In this method, palladium ions were adsorbed on Fe3O4&at;PDA surfaces through immersion of the Fe3O4&at;PDA into a palladium plating bath. The structure, morphology and physicochemical features of the prepared particles were studied using various analytical methods including high resolution transmission electron microscopy (HR-TEM), field emission scanning electron microscope (FESEM), energy-dispersive X-ray spectroscopy (EDS), vibrating sample magnetometer (VSM), X-ray photoelectron spectroscopy (XPS), inductively coupled plasma (ICP), thermogravimetric analysis (TGA) and FT-IR spectroscopy. Core–shell Fe3O4&at;PDA/Pd(II) nanoparticles showed excellent catalytic performance as a reusable nanocatalyst in Pd-catalyzed Buchwald–Hartwig C–N cross coupling reaction. A variety of aryl amines were prepared through reaction of aryl halides (chloride, bromide and iodide) and amines in high yields. The catalyst can be recycled and reapplied up to six cycles with no considerable change in its catalytic activity.
- Hemmati, Saba,Sarachegol, Pegah,Veisi, Hojat
-
-
- Dendrimer-encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe3O4@SiO2 nanoparticles as a novel recyclable catalyst for N-arylation of nitrogen heterocycles and green synthesis of 5-substituted 1H-tetrazoles
-
In this study, dendrimer-encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe3O4@SiO2 nanoparticles were prepared via a multistep-synthesis. Then, the synthesized composite was fully characterized by various techniques such as fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), dynamic light scattering (DLS), UV-vis spectroscopy, energy dispersive X-ray analysis (EDX), thermogravimetric analysis (TGA) and vibration sample magnetometer (VSM). From the information gained by. FE-SEM and TEM studies it can be inferred that the particles are mostly spherical in shape and have an average size of 50?nm. Also, the amount of Cu is determined to be 0.51?mmol/g in the catalyst by inductively coupled plasma (ICP) analyzer. This magnetic nano-compound has been successfully applied as a highly efficient, magnetically recoverable and stable catalyst for N-arylation of nitrogen heterocycles with aryl halides (I, Br) and arylboronic acids without using external ligands or additives. The catalyst was also employed in a one-pot, three-component reaction for the efficient and green synthesis of 5-substituted 1H-tetrazoles using various aldehydes, hydroxylamine hydrochloride and sodium azide in water. The magnetic catalyst can be easily separated by an external magnet bar and is recycled seven times without significant loss of its activity.
- Esmaeilpour, Mohsen,Sardarian, Ali Reza,Firouzabadi, Habib
-
-
- Rh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide
-
A Rh(III)-catalyzed C-H activation of boronic acid with aryl azide to obtain unsymmetric carbazoles, 1H-indoles, or indolines has been developed. The reaction constructs dual distinct C-N bonds via sp2/sp3 C-H activation and rhodium nitrene insertion. Synthetically, this approach represents an access to widely used carbazole derivatives. The practical application to CBP and unsymmetric TCTA derivatives has also been performed. Mechanistic experiments and DFT calculations demonstrate that a five-membered rhodacycle species is the key intermediate.
- Xu, Shiyang,Huang, Baoliang,Qiao, Guanyu,Huang, Ziyue,Zhang, Zhen,Li, Zongyang,Wang, Peng,Zhang, Zhenhua
-
supporting information
p. 5578 - 5582
(2018/09/25)
-