- New Pyrrole-Based Organic Dyes for Dye-Sensitized Solar Cells: Convenient Syntheses and High Efficiency
-
Harvesting the sunshine : Two new pyrrole-containing organic dyes were rationally designed and easily prepared. Thanks to the special electronic properties of pyrrole moieties and the introduction of the non-coplanar aromatic rings through a single bond (
- Li, Qianqian,Lu, Lanlan,Zhong, Cheng,Huang, Jing,Huang, Qing,Shi, Jie,Jin, Xianbo,Peng, Tianyou,Qin, Jingui,Li, Zhen
-
-
Read Online
- A novel electrochromic polymer containing triphenylamine derivative and pyrrole
-
A novel conducting polymer was successfully synthesized via electropolymerization of N1,N4-bis(4-(1H-pyrrol-1-yl) phenyl)-N1,N4-diphenylbenzene-1,4-diamine (DPTPA). This polymer film exhibited six various colors
- Ouyang, Mi,Wang, Genghao,Zhang, Cheng
-
-
Read Online
- A solvent-free manganese(II) -catalyzed Clauson-Kaas protocol for the synthesis of N-aryl pyrroles under microwave irradiation
-
The first manganese-catalyzed modified Clauson-Kaas reaction for N-substituted pyrrole synthesis using 2,5-dimethoxytetrahydrofuran with variously substituted aromatic amines has been developed (up to 89% yield). This interesting neat strategy is free from additives including co-catalysts, ligands, and acids. Relatively low cost, environmentally benign, and handy Mn(NO3)2·4H2O is employed as the catalyst under microwave conditions with a very short reaction time (20?min). The above qualities attest to the green nature of this reaction.
- Rohit, Kizhakkekuttu Radhakrishnan,Meera, Gopinadh,Anilkumar, Gopinathan
-
supporting information
p. 194 - 200
(2021/10/12)
-
- AIE compound, preparation method and application in detection of organic amine
-
The invention relates to the technical field of fluorescent materials, in particular to an AIE compound, a preparation method thereof and application of the AIE compound in organic amine detection. The structural general formula of the AIE compound is sho
- -
-
Paragraph 0100-0105
(2021/06/23)
-
- A facile synthesis of 1-aryl pyrroles by clauson-Kaas reaction using oxone as a catalyst under microwave irradiation
-
A new and efficient methodology to synthesize N-substituted pyrrole derivatives by Clauson Kaas reaction employing Oxone as catalyst was developed. The transformation was performed in acetonitrile under microwave irradiation. This procedure has several advantages such as high yield, clean product formation, and short reaction time.
- Gullapelli, Kumaraswamy,Brahmeshwari,Ravichander
-
p. 143 - 148
(2019/03/21)
-
- Solvent Free Synthesis of N-Substituted Pyrroles Catalyzed by Calcium Nitrate
-
Moderated and mild way for synthesizing N-substituted pyrrole has been demonstrated herein. No solvents need to be used for this reaction, and instead, reactants themselves acted as a reaction medium. In fact, the reaction is carried out using catalytic amount of Ca(NO3)2.4H2O. The reaction conditions are selective and mild that helped to tolerate a wide variety of functional groups to give the desired products in good chemical yields.
- Wani, Rucha R.,Chaudhari, Hemchandra K.,Takale, Balaram S.
-
supporting information
p. 1337 - 1340
(2019/02/05)
-
- MICROCAPSULES AND PROCESSES FOR THEIR PREPARATION
-
The present invention provides microcapsules encapsulating hydrophilic or hydrophobic active agents in an inorganic shell, processes for their preparation and compositions comprising them.
- -
-
Page/Page column 33; 41; 42
(2019/06/11)
-
- Nickel-Catalyzed Synthesis of N-Substituted Pyrroles Using Diols with Aryl- and Alkylamines
-
Herein, nickel-catalyzed sustainable strategy for the synthesis of N-substituted pyrroles using butene-1,4-diols and butyne-1,4-diols with a series of aryl-, alkyl-, and heteroarylamines is reported. The catalytic protocol is tolerant of free alcohol, halide, alkyl, alkoxy, oxygen heterocycles, activated benzyl, and the pyridine moiety and resulted in up to 90% yield. Initial mechanistic studies involving defined nickel catalyst, determination of rate, and order of reaction including deuterium-labeling experiments were performed for pyrrole synthesis.
- Singh, Khushboo,Kabadwal, Lalit Mohan,Bera, Sourajit,Alanthadka, Anitha,Banerjee, Debasis
-
p. 15406 - 15414
(2019/01/04)
-
- Diels-Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts
-
With a strategy of the formation of benzynes by using diaryliodonium salts, a cycloaddition reaction of N-arylpyrroles with benzynes was reported. A wide range of bridge-ring amines with various substituents have been synthesized in moderate to excellent yields (35-96%). Furthermore, with a catalytic amount of TsOH·H2O, these amines can be converted into the corresponding N-phenylamine derivatives easily, which are potentially useful in photosensitive dyes.
- Chen, Huangguan,Han, Jianwei,Wang, Limin
-
supporting information
p. 354 - 363
(2018/02/19)
-
- Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles
-
A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis-aromatization sequence.
- Scalacci, Nicoló,Black, Gary W.,Mattedi, Giulio,Brown, Nicola L.,Turner, Nicholas J.,Castagnolo, Daniele
-
p. 1295 - 1300
(2017/08/09)
-
- Sustainable Pathways to Pyrroles through Iron-Catalyzed N-Heterocyclization from Unsaturated Diols and Primary Amines
-
Pyrroles are prominent scaffolds in pharmaceutically active compounds and play an important role in medicinal chemistry. Therefore, the development of new, atom-economic, and sustainable catalytic strategies to obtain these moieties is highly desired. Direct catalytic pathways that utilize readily available alcohol substrates have been recently established; however, these approaches rely on the use of noble metals such as ruthenium or iridium. Here, we report on the direct synthesis of pyrroles using a catalyst based on the earth-abundant and inexpensive iron. The method uses 2-butyne-1,4-diol or 2-butene-1,4-diol that can be directly coupled with anilines, benzyl amines, and aliphatic amines to obtain a variety of N-substituted pyrroles in moderate-to-excellent isolated yields.
- Yan, Tao,Barta, Katalin
-
p. 2321 - 2325
(2016/10/24)
-
- A novel and convenient method for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones; synthesis and mechanistic study
-
An efficient, regioselective synthesis has been developed for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones from readily available 1H-pyrroles by sequential dibromination and selective organometallic bromine/lithium exchange followed by reaction with benzophenone. Comparison of various N-substituents was shown to demonstrate the high tolerance of the transformation to functional groups. The structures of the new products were determined by spectroscopic methods and confirmed by single-crystal X-ray diffraction measurement. In addition, theoretical study of the reaction mechanism and selective functionalization of the endocyclic double bond were also presented.
- Faigl, Ferenc,Deák, Szilvia,Mucsi, Zoltán,Hergert, Tamás,Balázs, László,Sándor, Boros,Balázs, Barbara,Holczbauer, Tamás,Nyerges, Miklós,Mátrav?lgyi, Béla
-
p. 5444 - 5455
(2016/08/04)
-
- Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium-zinc base and regioselectivity-computed CH acidity relationship
-
The synthesis of N-arylated pyrroles and indoles is documented, as well as their functionalization by deprotonative metallation using the base in situ prepared from LiTMP and ZnCl2·TMEDA (1/3 equiv). With N-phenylpyrrole and -indole, the reactions were carried out in hexane containing TMEDA which regioselectively afforded the 2-iodo derivatives after subsequent iodolysis. With pyrroles and indoles bearing N-substituents such as 2-thienyl, 3-pyridyl, 4-methoxyphenyl and 4-bromophenyl, the reactions all took place on the substituent, at the position either adjacent to the heteroatom (S, N) or ortho to the heteroatom-containing substituent (OMe, Br). The CH acidities of the substrates were determined in THF solution using the DFT B3LYP method in order to rationalize the experimental results.
- Messaoud, Mohamed Yacine Ameur,Bentabed-Ababsa, Ghenia,Hedidi, Madani,Derdour, A?cha,Chevallier, Floris,Halauko, Yury S.,Ivashkevich, Oleg A.,Matulis, Vadim E.,Picot, Laurent,Thiéry, Valérie,Roisnel, Thierry,Dorcet, Vincent,Mongin, Florence
-
supporting information
p. 1475 - 1485
(2016/04/19)
-
- Identification of Noncompetitive Inhibitors of Cytosolic 5′-Nucleotidase II Using a Fragment-Based Approach
-
We used a combined approach based on fragment-based drug design (FBDD) and in silico methods to design potential inhibitors of the cytosolic 5′-nucleotidase II (cN-II), which has been recognized as an important therapeutic target in hematological cancers. Two subgroups of small compounds (including adenine and biaryl moieties) were identified as cN-II binders and a fragment growing strategy guided by molecular docking was considered. Five compounds induced a strong inhibition of the 5′-nucleotidase activity in vitro, and the most potent ones were characterized as noncompetitive inhibitors. Biological evaluation in cancer cell lines showed synergic effect with selected anticancer drugs. Structural studies using X-ray crystallography lead to the identification of new binding sites for two derivatives and of a new crystal form showing important domain swapping. Altogether, the strategy developed herein allowed identifying new original noncompetitive inhibitors against cN-II that act in a synergistic manner with well-known antitumoral agents.
- Marton, Zsuzsanna,Guillon, Rémi,Krimm, Isabelle,Preeti,Rahimova, Rahila,Egron, David,Jordheim, Lars P.,Aghajari, Nushin,Dumontet, Charles,Périgaud, Christian,Lionne, Corinne,Peyrottes, Suzanne,Chaloin, Laurent
-
p. 9680 - 9696
(2016/01/12)
-
- Functionalized multi-walled carbon nanotubes as an efficient reusable heterogeneous catalyst for green synthesis of N-substituted pyrroles in water
-
In this protocol, the functionalization of multi-walled carbon nanotubes (MWCNTs) was carried out and the resulting sulfonated MWCNTs were characterized by FT-IR, XRD, SEM, BET, EDX, XPS and Raman spectroscopy that are each discussed separately in the text. Then, the MWCNT-SO3H composite was applied as an efficient, recyclable heterogeneous catalyst for the synthesis of N-substituted pyrroles via the reaction of 2,5-dimethoxy tetrahydrofuran with primary amines under clean and mild conditions. In this reaction, the N-substituted pyrroles were obtained as beneficial and significant products in short reaction times (30-65 min) and good to excellent yields (40-92%) with high purity. The products were obtained through a simple work up procedure and characterized by FT-IR, 1H NMR and 13C NMR. After the end of the reaction, the nanocatalyst was recovered and reused several times without efficient loss of its activity for the preparation of N-substituted pyrroles.
- Naeimi, Hossein,Dadaei, Mahla
-
p. 76221 - 76228
(2015/09/28)
-
- Copper-catalysed N-arylation of pyrrole with aryl iodides under ligand-free conditions
-
A simple, inexpensive and ligand-free copper-catalysed N-arylation of pyrrole with aryl iodides has been developed giving N-arylated products in moderate to excellent yields. The catalyst loading is relative low (5 mol%) and the catalyst system was stable in air.
- Liu, Lili,Wu, Fengtian,Liu, Yan,Xie, Jianwei,Dai, Bin,Zhou, Zhuoqiang
-
p. 180 - 182
(2014/04/17)
-
- Nano sulfated titania as a heterogeneous solid acid catalyst for the synthesis of pyrroles by clauson-kaas condensation under solvent-free conditions
-
A new and environmentally benign method for the preparation of N-substituted pyrroles from one-pot condensation reaction of 2,5-dimethoxytetrahydrofuran with amines and diamines in the presence of nano sulfated titania under solvent-free conditions is presented. This new protocol features simple operation, easy availability, stability, and eco-friendliness of catalyst, as well as high to excellent yields of products. In addition, we report for the first time an alternative method for the synthesis of pyrroles from aromatic amines containing the β-lactam fragment using nano sulfated titania as catalyst.
- Hosseini-Sarvari,Najafvand-Derikvandi,Jarrahpour,Heiran
-
p. 1732 - 1739
(2014/05/06)
-
- L-(+)-Tartaric acid and choline chloride based deep eutectic solvent: An efficient and reusable medium for synthesis of N-substituted pyrroles via Clauson-Kaas reaction
-
l-(+)-Tartaric acid-choline chloride based deep eutectic solvent has been found to be an effective promoted medium for Clauson-Kaas reaction of aromatic amines and 2,5-dimethoxytetrahydrofuran. Structurally diverse N-substituted pyrroles were obtained in high to excellent yields under mild conditions. The deep eutectic solvent is inexpensive, non-toxic, reusable and biodegradable.
- Wang, Ping,Ma, Fei-Ping,Zhang, Zhan-Hui
-
p. 259 - 262
(2014/11/07)
-
- Synthesis of pyrrole derivatives from diallylamines by one-pot tandem ring-closing metathesis and metal-catalyzed oxidative dehydrogenation
-
A series of aryl-substituted pyrrole derivatives was synthesized from diallylamines through a ruthenium carbene catalyzed ring-closing metathesis reaction and in situ oxidative dehydrogenation reaction catalyzed by FeCl 3·6H2O or CuCl2·2H2O in the presence of O2. The reaction was mild, simple, and convenient. An oxygen atmosphere played a critical role in obtaining high conversion of substituted pyrroles in the proposed catalytic system.
- Chen, Weiqiang,Wang, Jianhui
-
supporting information
p. 1958 - 1963
(2013/05/08)
-
- Squaric acid catalyzed simple synthesis of N-substituted pyrroles in green reaction media
-
An operationally simple and efficient protocol for squaric acid catalyzed synthesis of N-substituted pyrroles via the reaction of 2,5- dimethoxytetrahydrofuran and 2,5-hexandione with aryl amines in green reaction media (water, deep eutectic solvent, and polyethylene glycol) under ultrasound irradiation or thermal conditions in good to excellent yields has been developed.
- Azizi, Najmadin,Davoudpour, Anahita,Eskandari, Farshid,Batebi, Ehlham
-
p. 405 - 409
(2013/05/09)
-
- A recyclable magnetic nanoparticles supported antimony catalyst for the synthesis of N-substituted pyrroles in water
-
A new magnetic nanoparticle-supported antimony catalyst was prepared and evaluated as a recoverable catalyst for Clauson-Kaas reaction. The reaction proceeds efficiently in aqueous medium to give the corresponding N-substituted pyrroles in high yield. The immobilized catalyst could be easily recovered by magnetic separation and recycled for six times without significant loss of its catalytic activity.
- Ma, Fei-Ping,Li, Pei-He,Li, Bao-Le,Mo, Li-Ping,Liu, Ning,Kang, Hui-Jun,Liu, Ya-Nan,Zhang, Zhan-Hui
-
-
- Novel approach for the synthesis of N-Substituted pyrroles starting directly from nitro compounds in water
-
A novel approach for a facile high-yielding synthesis of N-substituted pyrroles has been discovered by the treatment of nitroarenes with 2,5-dimethoxytetrahydrofuran using indium in dilute aqueous HCl at room temperature. Taylor & Francis Group, LLC.
- Das, Biswanath,Shinde, Digambar Balaji,Kanth, Boddu Shashi,Kumar, Jayprakash Narayan
-
p. 548 - 553
(2011/11/29)
-
- Structure property relationships based on phenyl-1H-pyrrole end-capped thiophene semiconductors
-
Thiophene oligomers end-capped with phenyl-1H-pyrrole were used as active layers of organic field-effect transistors. Two types of cores that vary in size and shape of-linked thiophenes and fused-ring thiophenes were chosen to study the structureproperty
- Liu, Ying,Zhang, Ji,Liu, Yunqi,Yu, Gui,Ge, Ziyi
-
p. 1252 - 1256,5
(2020/09/09)
-
- Synthesis and characterization of novel second-order NLO-chromophores bearing pyrrole as an electron donor group
-
Two series of novel push-pull 1-(4-(thiophen-2-yl)phenyl)-1H-pyrroles 3-5 were designed to explore the consequence of using different electron accepting moieties linked to the thiophene at the arylthiophene bridge or to the pyrrole heterocycle, which plays the role of donor group. Compound 2 showed a different reactivity behavior in the presence of the Vilsmeier reagent or with tetracyanoethylene (TCNE) giving compounds 4a and 4b functionalized, respectively, at the 2 or on the 3-position of the pyrrole heterocycle. Their optical (linear and first hyperpolarizability), electrochemical, and thermal properties have been examined. Hyper-Rayleigh scattering (HRS) in dioxane solutions using a fundamental wavelength of 1064 nm was employed to evaluate their second-order nonlinear optical properties. Of these systems, thiobarbituric acid derivative 5b functionalized in the thiophene ring exhibits the largest first hyperpolarizability (β=2480×10-30 esu, T convention) compared to the corresponding compound 4c substituted on the pyrrole heterocycle (β=290×10-30 esu, T convention). Good to excellent thermal stabilities were also obtained for push-pull compounds 4 and 5 (270-288 °C). This multidisciplinary study shows that modulation of the optical and electronic properties can be achieved by introduction of the acceptor groups in the thiophene of the arylthiophene bridge. The measured molecular first hyperpolarizabilities and the observed electrochemical behavior are quite sensitive to the position of acceptor group on the heterocyclic system (on the thiophene or on the pyrrole ring) as well as the strength of the acceptor moieties. Moreover, the combination of their good nonlinearity and high thermal stability make them good candidates for second-order nonlinear optical applications.
- Castro, M. Cidália R.,Belsley,Fonseca, A. Maurício C.,Raposo, M. Manuela M.
-
scheme or table
p. 8147 - 8155
(2012/09/22)
-
- Synthesis of N-substituted pyrroles under catalyst-and solvent-free conditions
-
N-Substituted pyrroles were synthesized under neat conditions by the reaction of aromatic amines with 2, 5-dimethoxytetrahydrofuran in excellent yields.
- Ramesh, Katla,Murthy, Sabbavarapu Narayana,Nageswar, Yadavalli Venkata Durga
-
experimental part
p. 2471 - 2477
(2012/06/29)
-
- Unique chemoselective Clauson-Kass reaction of substituted aniline catalyzed by MgI2 etherate
-
Clauson-Kass reaction of various substituted aniline, primary aryl amide, and sufonyl amide with 2,5-dimethoxytetrahydrofuran was realized in the presence of 10 mol % of MgI2 etherate in a mild, efficient, and highly chemoselective manner. Iodide counterion and solvents (i.e., MeCN) played the critical roles for the unique reactivity of this catalytic system.
- Zhang, Xingxian,Shi, Junchen
-
experimental part
p. 898 - 903
(2011/03/19)
-
- C-N bond formation catalysed by CuI Bonded to polyaniline nanofiber
-
Polyaniline nanofiber as a macroligand for the supported cuprous iodide catalyst (CuI-PANInf) has been developed for the coupling of aryl halides (including aryl chlorides) with aliphatic, aromatic, and N(H)-heterocyclic amines under ambient conditions (80 °C for aryl chlorides) has been developed. This simple and efficient method for coupling reactions is highly versatile, convenient, and also the catalyst can be used for several cycles with good-to-excellent yields.
- Arundhathi, Racha,Kumar, Desitti Chaitanya,Sreedhar, Bojja
-
supporting information; experimental part
p. 3621 - 3630
(2010/08/20)
-
- Crystal structure and optical properties of n-pyrrole end-capped thiophene/phenyl co-oligomer: Strong h-type excitonic coupling and emission self-waveguiding
-
In view of their exploitation in working devices, mainly for their emission properties, the interest in crystals of thiophene/phenylene co-oligomers has recently increased. Here, we describe the strategies for the organic synthesis and crystal growth of a
- Tavazzi, Silvia,Miozzo, Luciano,Silvestri, Leonardo,Mora, Stefano,Spearman, Peter,Moret, Massimo,Rizzato, Silvia,Braga, Daniele,Diagne Diaw, Abdou Karim,Gningue-Sall, Diariatou,Aaron, Jean-Jacques,Yassar, Abderrahim
-
scheme or table
p. 2342 - 2349
(2011/11/13)
-
- Facile cuI-catalyzed arylation of azoles and amides using simple enaminones as efficient ligands
-
(E)-3-(Dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one was found to be an excellent ligand for copper-catalyzed N-arylation of azoles and amides with aryl halides under mild conditions. The reaction took place at 82 C in MeCN with broad functional-group compatibility. A combination of the ligand and CuI proved to be an efficient catalytic system to promote the coupling reactions of aryl halides with azoles and amides.
- Cheng, Cungui,Sun, Gonglei,Wan, Jieping,Sun, Cuirong
-
experimental part
p. 2663 - 2668
(2010/01/16)
-
- Iron-catalyzed inexpensive and practical synthesis of N-substituted pyrroles in water
-
An operationally simple, practical, and economical protocol for iron(III) chloride catalyzed Paal-Knorr pyrrole synthesis in water in good to excellent yields has been developed. Several N-substituted pyrroles are readily prepared from the reaction of 2,5-dimethoxytetrahydrofuran and aryl/alkyl, sulfonyl and acyl amines under very mild reaction conditions. Georg Thieme Verlag Stuttgart.
- Azizi, Najmedin,Khajeh-Amiri, Alireza,Ghafuri, Hossein,Bolourtchian, Mohammad,Saidi, Mohammad Reza
-
experimental part
p. 2245 - 2248
(2009/12/03)
-
- Iron/copper-cocatalyzed ullmann N,O-arylation using FeCl3, CuO, and rac-1,1′-Binaphthyl-2,2′-diol
-
We have developed an efficient and inexpensive bimetallic catalyst FeCl3, CuO, and rac-BINOL that could promote N,O-arylation of aliphatic, arylamines, and phenols. The cross-coupling reaction conditions have high tolerance of various functional groups. This versatile and efficient iron/copper-cocatalyst can widely be used in the synthesis of the compounds containing (aryl)C-N or (aryl)C-O(aryl) bond. Georg Thieme Verlag Stuttgart.
- Wang, Zhe,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
-
body text
p. 2540 - 2546
(2009/04/12)
-
- N,N′-(Phenylmethylene)diacetamide analogues as economical and efficient ligands in copper-catalyzed arylation of aromatic nitrogen-containing heterocycles
-
N,N′-(Phenylmethylene)diacetamide analogues which were simply prepared from the condensation reaction of an aldehyde with an amide or urea were found to be efficient ligands in copper-catalyzed coupling reaction of aryl halides with various azole nucleophiles. The newly developed ligand showed broad application scope in this conversion. Compounds including imidazoles, benzoimidazoles, pyrrole, indole, and benzotriazole were successfully arylated with diversified aromatic halides to give corresponding products in moderate to excellent yields. Georg Thieme Verlag Stuttgart.
- Wan, Jie-Ping,Chai, Yun-Feng,Wu, Jian-Mei,Pan, Yuan-Jiang
-
experimental part
p. 3068 - 3072
(2009/06/28)
-
- Effects of N-pyrrole substitution on the anti-biofilm activities of oroidin derivatives against Acinetobacter baumannii
-
Bacteria of the genus Acinetobacter spp. are rapidly emerging as problematic pathogens in healthcare settings. This is exacerbated by the bacteria's ability to form robust biofilms. Marine natural products incorporating a 2-aminoimidazole (2-AI) motif, namely from the oroidin class of marine alkaloids, have served as a unique scaffold for developing molecules that have the ability to inhibit and disperse bacterial biofilms. Herein we present the anti-biofilm activity of a small library of second generation oroidin analogues against the bacterium Acinetobacter baumannii.
- Richards, Justin J.,Reed, Catherine S.,Melander, Christian
-
supporting information; scheme or table
p. 4325 - 4327
(2009/04/06)
-
- Practical copper-catalyzed N-arylation of nitrogen heterocycles with aryl halides under ligand and additive free conditions
-
N-arylation of a wide variety of nitrogen heterocycles with aryl iodides catalyzed by copper iodide under mild ligand and additive free conditions (nBu4NBr, PhMe, NaOH, reflux, 22 h) was accomplished in good to excellent yields (up to 95%) and substrate conversions (up to 99%).
- Chang, Joyce Wei Wei,Xu, Xiuhui,Chan, Philip Wai Hong
-
p. 245 - 248
(2007/10/03)
-
- CuBr/rac-BINOL-catalyzed N-arylations of aliphatic amines at room temperature
-
We have developed an efficient and readily available catalyst system CuBr/racemic BINOL ( 1,1′-binaphthyl-2,2′-diol) that catalyzes N-arylation of aliphatic amines at room temperature, and this inexpensive catalyst system is of high selectivity and tolerance toward various functional groups in the substrates.
- Jiang, Deshou,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
-
p. 672 - 674
(2007/10/03)
-
- Crystallography and magnetism of two 1-(4-nitroxylphenyl)pyrroles
-
(Figure Presented) Stable radicals 1-(4-(N-tert-butyl-N-amnoxyl)phenyl) pyrrole (BNPP) and 1-(4-(N-[para-methoxyphenyl]-N-aminoxyi)phenyl)pyrrole (MNPP) were, synthesized and characterized by crystallography and magnetism. BNPP crystals exhibit 1-D chains
- Delen, Zeynep,Lahti, Paul M.
-
p. 9341 - 9347
(2007/10/03)
-
- Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles
-
CuI-catalyzed coupling reaction of electron-deficient aryl iodides with aliphatic primary amines occurs at 40 °C under the promotion of N-methylglycine. Using L-proline as the promoter, coupling reaction of aryl iodides or aryl bromides with aliphatic primary amines, aliphatic cyclic secondary amines, or electron-rich primary arylamines proceeds at 60-90 °C; an intramolecular coupling reaction between aryl chloride and primary amine moieties gives indoline at 70 °C; coupling reaction of aryl iodides with indole, pyrrole, carbazole, imidazole, or pyrazole can be carried out at 75-90 °C; and coupling reaction of electron-deficient aryl bromides with imidazole or pyrazole occurs at 60-90 °C to provide the corresponding N-aryl products in good to excellent yields. In addition, N,N-dimethylglycine promotes the coupling reaction of electron-rich aryl bromides with imidazole or pyrazole to afford the corresponding N-aryl imidazoles or pyrazoles at 110 °C. The possible action of amino acids in these coupling reactions is discussed.
- Zhang, Hui,Cai, Qian,Ma, Dawei
-
p. 5164 - 5173
(2007/10/03)
-
- L-Proline Promoted Ullmann-Type Coupling Reactions of Aryl Iodides with Indoles, Pyrroles, Imidazoles or Pyrazoles
-
The Ullmann-type coupling reactions of aryl iodides and several nitrogen heterocycles occur at 80-90°C with L-proline as additive, giving N-arylpyrroles, N-arylindoles, N-arylimidazoles, and N-pyrazoles in good to excellent yields.
- Ma, Dawei,Cai, Qian
-
p. 128 - 130
(2007/10/03)
-
- Design and preparation of pyrrole-based spin-polarized donors
-
As a fundamental building block of a conductive magnetic macromolecule, a series of pyrrole derivatives carrying a nitronyl nitroxide (NN) group was prepared. Some of these derivatives afforded ground-state triplet diradical cations upon one-electron oxid
- Nakazaki, Jotaro,Chung, InGwon,Matsushita, Michio M.,Sugawara, Tadashi,Watanabe, Ryoji,Izuoka, Akira,Kawada, Yuzo
-
p. 1011 - 1022
(2007/10/03)
-
- Solvent and ligand effects on selective mono- and dilithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles
-
Novel methods for site-selective lithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles are described. Mono- or dilithiations are governed by change of both the temperature and the solvent from tetrahydrofuran to diethyl ether. Regioselectiv
- Fogassy, Katalin,Kovacs, Krisztina,Keseru, Gyoergy M.,Toke, Laszlo,Faigl, Ferenc
-
p. 1039 - 1043
(2007/10/03)
-
- Synthesis and nuclear magnetic resonance spectroscopic studies of 1- arylpyrroles
-
A series of m- and p-substituted 1-phenyl, 1-benzyl, 1-benzoyl, and 1- (2-phenylethyl)pyrroles was prepared and their 1H and 13C nmr spectroscopic characteristics were examined. In general, good correlations were observed between the chemical shift values of the β-H and the β-C of pyrroles [except 1-(2-phenylethyl)pyrroles] and the Hammettt σ. The observation may be explained in terms of the electronic effects of the substituents which are transmitted through bonds and through space by interaction of the p orbitals between β-Cs of the pyrrole ring and m- and p- Cs of the phenyl ring. Substituent constants of 1-pyrrolyl, 1-pyrrolylmethyl, and 1-pyrroloyl groups for the 1H and 13C chemical shifts of phenyl ring are also presented.
- Lee, Chang Kiu,Jun, Jung Ho,Yu, Ji Sook
-
-