- Utilization of caffeine carbon supported cobalt catalyst in the tandem synthesis of pyrroles from nitroarenes and alkenyl diols
-
Employing bio-waste caffeine carbon-supported heterogeneous cobalt catalyst, synthesis of various substituted pyrrole derivatives is reported. In this methodology, pyrroles were synthesized through coupling between nitroarenes and alkenyl diols in a tandem manner. Among all the heterogeneous catalysts Co(OAc)2-CC-800 displayed the highest catalytic activity. Preparative scale synthesis of pyrroles and synthesis of anti-tubercular agent 5-(4-(1H-pyrrol-1-yl)phenyl)-1,3,4-oxadiazole-2-thiol revealed the practical applicability of this protocol. Several kinetic experiments and Hammett studies were conducted to understand the probable mechanism and electronic effects on this transformation.
- Balasubramaniam, Bhuvaneshwari,Dhara, Partha,Gupta, Raju K.,Kundu, Sabuj,Panja, Dibyajyoti,Sau, Anirban
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p. 244 - 254
(2021/09/07)
-
- Visible-Light-Induced, Base-Promoted Transition-Metal-Free Dehalogenation of Aryl Fluorides, Chlorides, Bromides, and Iodides
-
We report a simple and efficient visible-light-induced transition-metal-free hydrogenation of aryl halides. The combined visible light and base system is used to initiate the desired radical-mediated hydrogenation. A variety of aryl fluorides, chlorides, bromides, and iodides could be reduced to the corresponding (hetero)arenes with excellent yields under mild conditions. Various functional groups and other heterocyclic compounds are tolerated.
- Ding, Ting-Hui,Qu, Jian-Ping,Kang, Yan-Biao
-
supporting information
p. 3084 - 3088
(2020/04/10)
-
- Synergistic catalysis for light-driven proton reduction using a polyoxometalate-based Cu-Ni heterometallic-organic framework
-
Synergistic effects of bimetallic Ni and Cu supported on metal-organic polymer composites based on Wells-Dawson P2W18O626- clusters as photosensitizer units were identified, and we report a novel approach for addressing these issues for dehydrogenation and hydrogen production reactions.
- Sun, Wenlong,He, Cheng,Liu, Tao,Duan, Chunying
-
supporting information
p. 3805 - 3808
(2019/04/01)
-
- 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)
-
- 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)
-
- 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)
-
- Pd/Cu-catalyzed dual C-H bond carbonylation towards the synthesis of fluorazones
-
Pd/Cu catalyzed oxidative dual C-H bond activation/carbonylation still remains a great challenge due to the generation of by-products via C-C bond formation. Herein we developed a straightforward Pd/Cu-catalyzed oxidative dual C-H bond carbonylation process to access biologically and pharmaceutically important fluorazones from easily available N-aryl pyrroles and CO. A wide range of functional groups were well tolerated in this transformation, and O2 could be utilized as the only terminal oxidant to promote the oxidative carbonylation process.
- Liao, Fan,Shi, Renyi,Sha, Yuchen,Xia, Jianhui,Liao, Weilin,Lei, Aiwen
-
supporting information
p. 4354 - 4357
(2017/04/21)
-
- 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)
-
- Efficient and recyclable copper-based MOF-catalyzed N-arylation of N-containing heterocycles with aryliodides
-
Copper-based MOF-199 was used as an efficient heterogeneous catalyst to catalyze cross-coupling reactions between N-containing heterocycles and aryliodides with high yields. The catalyst can be easily separated from the reaction mixture, and can be reused at least 5 times without significantly decreasing the activity. The XRD results showed that the crystallinity and structure of MOF-199 can be maintained well during the coupling reaction.
- Li, Zihao,Meng, Fei,Zhang, Jie,Xie, Jianwei,Dai, Bin
-
supporting information
p. 10861 - 10865
(2016/12/06)
-
- 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)
-
- 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)
-
- Synthesis of polysubstituted pyrroles via Pd-catalyzed oxidative alkene C-H bond arylation and amination
-
A novel Pd(II)-catalyzed oxidative approach to construct polysubstituted pyrroles from N-homoallylicamines and arylboronic acids was developed. This transformation is supposed to proceed through cascade formation of C-C and C-N bonds via oxidative arylation of unactive alkenes, followed by intramolecular aza-Wacker cyclization.
- Zheng, Jia,Huang, Liangbin,Huang, Chuyu,Wu, Wanqing,Jiang, Huanfeng
-
p. 1235 - 1242
(2015/01/30)
-
- 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)
-
- 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)
-
- 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)
-
- Facial preparation of sulfonic acid-functionalized magnetite-coated maghemite as a magnetically separable catalyst for pyrrole synthesis
-
The synthesis, characterization, an Copyright
- Mahmoudi, Hajar,Jafari, Abbas Ali
-
p. 3743 - 3749
(2014/01/06)
-
- 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
-
-
- 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)
-
- 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)
-
- Octanuclear Cu(I)-dithiophosphates: An efficient catalyst system for N-arylation of azoles, amines, and amides
-
The formation of a C-N bond via the cross-couplings of aryl iodides with azoles, aryl amine, and amides can be successfully achieved in decent yield by the utilization of both [Cu8(H){S2P(OiPr) 2}6]+ and [Cu8{S2P(OEt) 2}6]2+ as the pre-catalysts.
- Wu, Cheng-Chieh,Lee, Bo-Han,Liao, Ping-Kuei,Fang, Ching-Shiang,Liu
-
experimental part
p. 480 - 484
(2012/07/30)
-
- 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)
-
- Assisted tandem catalytic RCM-aromatization in the synthesis of pyrroles and furans
-
An assisted tandem catalytic transformation of diallyl amines and diallyl ethers into N-aryl pyrroles and furans, respectively, is described. The sequence relies on ring closing metathesis followed by dehydrogenation of the initially formed dihydropyrroles and dihydrofurans. Both steps are Ru-catalyzed, but the sequence requires only one precatalyst, because conversion of the metathesis catalyst into the dehydrogenation catalyst is achieved in situ, triggered by the oxidant tert-butyl hydroperoxide.
- Schmidt, Bernd,Krehl, Stefan,Jablowski, Eric
-
p. 5119 - 5130
(2012/08/07)
-
- A versatile and efficient cu-catalyzed N-Arylation of aromatic cyclic secondary amines with aryl halides
-
A copper-catalyzed coupling reaction of aryl halides with various aromatic cyclic secondary amines in DMSO has been developed efficiently. The versatile and efficient copper catalyst system is of wide-spread and practical application in cross-coupling reactions.
- Yang, Haitao,Miao, Zhiwei,Chen, Ruyu
-
experimental part
p. 325 - 331
(2012/05/31)
-
- Cross-coupling reactions of aryl halides with amines, phenols, and thiols catalyzed by an N,N′-dioxide-copper(I) catalytic system
-
The coupling reactions of various N, O, and S nucleophilic reagents with aryl halides have been successfully carried out under mild conditions by using a novel chiral N,N′-dioxide-copper(I) catalytic system as the catalyst. This versatile and efficient catalyst system has been demonstrated to facilitate the cross-coupling reactions of aryl halides with amines, phenols, and thiols to afford the corresponding desired products in good to excellent yields.
- Yang, Haitao,Xi, Chao,Miao, Zhiwei,Chen, Ruyu
-
supporting information; experimental part
p. 3353 - 3360
(2011/08/03)
-
- A manganese/copper bimetallic catalyst for C-N coupling reactions under mild conditions in water
-
An efficient and convenient bimetallic MnF2/CuI catalyst in combination with trans-1,2-diaminocyclohexane has been developed for the cross-coupling of nitrogen heterocycles with aryl halides in water at moderate temperature. A variety of nitrogen nucleophiles including pyrazole, 7-azaindole, indazole, indole, pyrrole and imidazole afforded the corresponding products in moderate to good yields (up to 94%) under the described arylation conditions.
- Teo, Yong-Chua,Yong, Fui-Fong,Lim, Gina Shiyun
-
supporting information; experimental part
p. 7171 - 7174
(2012/01/05)
-
- A ligand-free copper(I) oxide catalyzed strategy for the N-arylation of azoles in water
-
A simple and practical protocol has been developed for the cross-coupling of azoles and aryl iodides under ligand-free copper(I) oxide catalyzed conditions in water. The protocol uses tetrabutylammonium bromide (TBAB) as the phase-transfer catalyst, and water as the solvent, and shows good tolerance towards various functional groups.
- Yong, Fui-Fong,Teo, Yong-Chua,Tay, Siew-Hoon,Tan, Bryan Yong-Hao,Lim, Kim-Huat
-
supporting information; experimental part
p. 1161 - 1164
(2011/03/21)
-
- Tungstophosphoric acid supported on silica gel (H3PW 12O40/SiO2) as an eco-friendly, reusable and heterogeneous catalyst for the synthesis of pyrroles in solution or under solvent-free microwave irradiation
-
Heteropoly acid supported on silica gel (H3PW12O 40/SiO2) is easily used as a heterogonous, reusable and efficient catalyst for the synthesis of N-substituted, 2- and 3-unsubstituted pyrroles in solution or under solvent-free microwave irradiation. The catalyst can be easily recovered and reused for several times without loss of activity.
- Jafari,Mahmoudi,Mirjalili
-
experimental part
p. 851 - 856
(2012/06/18)
-
- New strategy for the synthesis of N-aryl pyrroles: Cu-catalyzed C-N cross-coupling reaction of trans-4-hydroxy-l-proline with aryl halides
-
trans-4-Hydroxy-l-proline is used for the first time as an effective nucleophilic coupling partner with aryl halides mediated by copper iodide with Cs2CO3 as the base and DMSO as the solvent. Utilizing this protocol cross-coupling of trans-4-hydroxy-l-proline with a wide variety of substituted aryl halides to produce N-aryl pyrroles in moderate to good yields.
- Reddy, V. Prakash,Kumar, A. Vijay,Rao, K. Rama
-
experimental part
p. 777 - 780
(2011/03/21)
-
- Oxazolidin-2-one as efficient ligand for the copper-catalyzed N- Arylation of pyrrole, imidazole and indole
-
Oxazolidin-2-one was found to be a facile ligand for the N-arylation of pyrrole, indole, and imidazole with aryl and heteroaryl iodides, bromides, and chlorides by applying Cul as catalyst. The easy preparation, commercial availability, lower molecular weight, and broad substrate applicability, as well as substituent compatibility of this catalysis system render oxazolidin-2-one great advantages over the Cu-catalyzed methods that have already been utilized in a number of applications.
- Ma, Hengchang,Wu, Shang,Sun, Qiangsheng,Lei, Ziqiang
-
experimental part
p. 212 - 218
(2011/07/07)
-
- Ligand-free CuCl-catalyzed C-N bond formation in aqueous media
-
CuCl-catalyzed N-arylation of alkyl amines and N-heterocycles with substituted aryl iodides and bromides can be carried out in 40% nBu4N+OH- aqueous solution without any ligands. Crown Copyright
- Xu, Hua-Jian,Zheng, Fa-Yin,Liang, Yu-Feng,Cai, Zhen-Ya,Feng, Yi-Si,Che, Da-Qing
-
experimental part
p. 669 - 671
(2010/04/23)
-
- CuCl-catalyzed formation of C-N bond with a soluble base
-
Tetramethylammonium hydroxide was used as a base instead of a traditional inorganic base in this copper-catalyzed system and some satisfactory results were obtained. Various functional groups were compatible under this reaction condition.
- Feng, Yi-Si,Man, Qiu-Shi,Pan, Pan,Pan, Zong-Qin,Xu, Hua-Jian
-
experimental part
p. 2585 - 2588
(2009/08/07)
-
- Copper-catalyzed C-N coupling of amides and nitrogen-containing heterocycles in the presence of cesium fluoride
-
The copper-catalyzed C-N coupling of amides to aryl halides usually requires the use of strong alkali metal bases, such as K2CO3, K3PO4, and Cs2CO3, at high temperature. We discovered that
- Phillips, Dean P.,Zhu, Xue-Feng,Lau, Thomas L.,He, Xiaohui,Yang, Kunyong,Liu, Hong
-
supporting information; experimental part
p. 7293 - 7296
(2010/03/03)
-
- 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)
-
- A microwave-assisted, green procedure for the synthesis of N-aryl sulfonyl and N-aryl pyrroles
-
A simplified approach to the uncatalyzed Paal-Knorr condensation using microwave irradiation in water is described.
- Wilson, Matthew A.,Filzen, Gary,Welmaker, Gregory S.
-
experimental part
p. 4807 - 4809
(2009/10/26)
-
- Scandium triflate-catalysed synthesis of N-substituted pyrroles from amine and 2,5-dimethoxytetrahydrofuran
-
The Clauson-Kass pyrrole synthesis catalysed by scandium triflate afforded N-substituted 2- and 3-unsubstituted pyrroles with yields ranged from good to excellent. Aromatic amines, heteroaomatic amines, 4-methylbenzenesulfonamide and 2-chlorobenzamide are good substrates in this transformation.
- Zuo, Bing,Chen, Jiuxi,Liu, Miaochang,Ding, Jinchang,Wu, Huayue,Su, Weike
-
experimental part
p. 14 - 16
(2009/09/25)
-
- 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)
-
- Highly practical "ligand-free-like" copper-catalyzed N-arylation of azoles in lower nitrile solvents
-
In lower nitrile solvents, the N-arylation of azoles with aryl halides was achieved efficiently in the presence of copper powder without any additional ligands. Thus, the first nitrile type of monodentate ligand-mediated, "ligand-free-like" copper-catalyzed N-arylation procedure was established.
- Zhu, Rui,Xing, Lixin,Wang, Xinyan,Cheng, Chuanjie,Su, Deyong,Hu, Yuefei
-
supporting information; experimental part
p. 1253 - 1257
(2009/06/18)
-
- N-hydroxyimides as efficient ligands for the copper-catalyzed N-arylation of pyrrole, imidazole, and indole
-
(Chemical Equation Presented) An experimentally simple, efficient, and inexpensive catalyst system was developed for the N-arylation of pyrroles, indoles, and imidazole with aryl and heteroaryl iodides, bro-mides, and chlorides by applying CuI as catalyst, N-hydroxysuccinimide (L1), N-hydroxymaleimide (L2), or N-hydroxyphthalimide (L3) as ligand, CH3ONa as base, and DMSO as solvent. A variety of functional groups are tolerated in the reaction, including those that are not compatible with Pd-catalyzed amidation methodology.
- Ma, Heng-Chang,Jiang, Xuan-Zhen
-
p. 8943 - 8946
(2008/03/12)
-
- 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)
-
- A mild and efficient method for copper-catalyzed Ullmann-type N-arylation of aliphatic amines and amino acids
-
An efficient and general protocol for copper-catalyzed N-arylation of aliphatic amines and amino acids has been developed using aryl iodides under mild conditions (coupling temperature at 25-35°C). For the N-(o-nitrophenyl) amino acid derivatives, subsequent reduction of the nitro group in the presence of tin(II) chloride resulted in 3,4-dihydroquinoxalin-2(1H)-one derivatives in good yields. Georg Thieme Verlag Stuttgart New York.
- Jiang, Qun,Jiang, Deshou,Jiang, Yuyang,Fu, Hua,Zhao, Yufen
-
p. 1836 - 1842
(2008/02/10)
-
- Microwave-assisted ring-closing metathesis of diallylamines: a rapid synthesis of pyrrole and pyrroline derivatives
-
The ring-closing metathesis (RCM) reactions of diallylamines occurred under controlled microwave irradiation. In addition to the high reaction rate, the key features of the reaction are that it can be carried out without deactivation of the substrates and
- Yang, Qian,Li, Xin-Yong,Wu, Hong,Xiao, Wen-Jing
-
p. 3893 - 3896
(2007/10/03)
-
- 13C- and 14C-labelling of N-[1-(4-chlorophenyl)-1H- pyrrol-2-yl-methyleneamino] guanidinium acetate
-
N-[1-(4-chlorophenyl)-1H-pyrrol-2-yl-13C4- methyleneamino]guanidinium acetate has been synthesized by a four-step procedure. This involved reduction of the Weinreb amide N,N′-dimethyl-N, N′-dimethyloxybutane-1,4-diamide-1,2,3,4-
- Almeida, Maria,Johannesson, Petra,Boman, Arne,Lundstedt, Torbjoern
-
p. 621 - 627
(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
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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
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- Reductive one batch synthesis of N-substituted pyrrolidines from primary amines and 2,5-dimethoxytetrahydrofuran
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The construction of the pyrrolidine ring about a nitrogen of a primary amine by a reductive condensation reaction using 2,5- dimethoxytetrahydrofuran and sodium borohydride in acidic water medium is described. The reaction is fast, affords good to excellent yields and appears insensitive to electron effects and severe steric hindrance; it is found to be compatible with a large variety of aryl substituents, including nitro and oxo groups. The reaction allows the introduction of two deuterium atoms, with label conservation, in both the α-positions of the pyrrolidine ring by the use of sodium borodeuteride instead of sodium borohydride.
- Verardo, Giancarlo,Dolce, Anna,Toniutti, Nicoletta
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- A facile synthesis of N-substituted pyrroles
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Phosphorous pentoxide is the catalyst of choice for the facile conversion of primary amines, aromatic amines, sulfonamides and primary amides into the corresponding N-substituted pyrroles from 2,5-dimethoxytetrahydrofuran.
- Fang,Leysen,Ottenheijm
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p. 1857 - 1861
(2007/10/02)
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- Intermolecular Thermal Reaction of Arylnitrenes with Furans
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4-Methoxy-, 4-chloro-, and 4-nitro-phenylnitrenes have been thermally generated by decomposition of the corresponding aryl azides in the presence of furan and a series of 2-substituted and 2,5-disubstituted furans. 4-Nitrophenylnitrene has been shown to be capable of undergoing electrophilic addition to the furan ring both at the α- and β-position, whereas only evidence of α-attack has been provided by 4-chlorophenylnitrene.On the other hand, no evidence of electrophilic attack has been obtained with 4-methoxyphenylnitrene, which affords only products ascribable to the triplet nitrene.The formation of a number of products ultimately resulting from nitrene attack at the α-position of the furan ring followed by a ring-opening process and the general occurrence of 1-(4-nitrophenyl)- and 1-(4-chlorophenyl)-1,2,3-triazole from thermolysis of 4-nitro- or 4-chloro-phenyl azide in the presence of the furans examined is discussed.
- Benati, Luisa,Montevecchi, Pier Carlo,Toselli, Maurizio,Spagnolo, Piero
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p. 1859 - 1864
(2007/10/02)
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- ELECTRON-DONATING PROPERTIES OF SOME N-ARYLPYRROOLES. I. CHARGE-TRANSFER COMPLEXES
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The complex formation between some N-arylpyrroles and the electron acceptors iodine, tetracyanoethylene, and chloranil has been investigated spectrophotometrically.Association constants, free energies of formation and other thermodynamic properties have been calculated for the charge-transfer complexes of these systems.Values of band maxima were used to calculate the ionisation potentials of the donors.Factors governing the stability of the molecular complexes studied are analysed and discussed.
- Abu-Eittah, Rafie H.,Hilal, Refat H.,El-Shall, Mohamed S.
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p. 487 - 492
(2007/10/02)
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