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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Review Article

Copper-Catalyzed N-Arylation of Indoles

Author(s): Kalathingal Nasreen Hisana, Cheriya Mukkolakkol Afsina Abdulla and Gopinathan Anilkumar*

Volume 26, Issue 9, 2022

Published on: 05 July, 2022

Page: [857 - 886] Pages: 30

DOI: 10.2174/1385272826666220527140651

Price: $65

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Abstract

Over the past decades, the N-arylation of indoles has gained an inevitable role in the fields of material science, pharmaceuticals, and agrochemical industries. They are the basic core skeleton of many natural products. Their synthesis by Ullmann-type C-N coupling reaction of indole derivatives with aryl halides through various catalytic protocols is well explored. Transition metal catalysis was the best method for synthesizing 1-aryl indoles, and copper catalysis is the leading among them. This review comprehends the recent developments in the copper-catalyzed C-N cross-coupling of indoles with aryl halides from 2010 to 2022.

Keywords: Copper, catalysis, N-Arylation, indole, aryl halides, ligand, nano-catalysis.

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[1]
Bandini, M.; Eichholzer, A. Catalytic functionalization of indoles in a new dimension. Angew. Chem. Int. Ed. Engl., 2009, 48(51), 9608-9644.
[http://dx.doi.org/10.1002/anie.200901843] [PMID: 19946913]
[2]
Lewis, R.; Bagnall, A-M.; Leitner, M. Sertindole for schizophrenia. Cochrane Database Syst. Rev., 2005, (3), CD001715.
[PMID: 16034864]
[3]
Vangrevelinghe, E.; Zimmermann, K.; Schoepfer, J.; Portmann, R.; Fabbro, D.; Furet, P. Discovery of a potent and selective protein kinase CK2 inhibitor by high-throughput docking. J. Med. Chem., 2003, 46(13), 2656-2662.
[http://dx.doi.org/10.1021/jm030827e] [PMID: 12801229]
[4]
Corbet, J.P.; Mignani, G. Selected patented cross-coupling reaction technologies. Chem. Rev., 2006, 106(7), 2651-2710.
[http://dx.doi.org/10.1021/cr0505268] [PMID: 16836296]
[5]
Kunz, K.; Scholtz, U.; Ganzer, D. Renaissance of Ullmann and Goldberg reactions-progress in copper catalyzed CN-, CO-and CS-coupling. Synlett, 2003, 15, 2428-2439.
[http://dx.doi.org/10.1055/s-2003-42473]
[6]
Herrmann, W.A. N-heterocyclic carbenes: A new concept in organometallic catalysis. Angew. Chem. Int. Ed., 2002, 41(8), 1290-1309.
[http://dx.doi.org/10.1002/1521-3773(20020415)41:8<1290:AID-ANIE1290>3.0.CO;2-Y] [PMID: 19750753]
[7]
Cozzi, P.; Carganico, G.; Fusar, D.; Grossoni, M.; Menichincheri, M.; Pinciroli, V.; Tonani, R.; Vaghi, F.; Salvati, P. Imidazol-1-yl and pyridin-3-yl derivatives of 4-phenyl-1,4-dihydropyridines combining Ca2+ antagonism and thromboxane A2 synthase inhibition. J. Med. Chem., 1993, 36(20), 2964-2972.
[http://dx.doi.org/10.1021/jm00072a017] [PMID: 8411014]
[8]
Monnier, F.; Taillefer, M. Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions: Copper makes a difference. Angew. Chem. Int. Ed. Engl., 2008, 47(17), 3096-3099.
[http://dx.doi.org/10.1002/anie.200703209] [PMID: 18381606]
[9]
Antilla, J.C.; Klapars, A.; Buchwald, S.L. The copper-catalyzed N-arylation of indoles. J. Am. Chem. Soc., 2002, 124(39), 11684-11688.
[http://dx.doi.org/10.1021/ja027433h] [PMID: 12296734]
[10]
Mann, G.; Hartwig, J.F.; Driver, M.S.; Fernández-Rivas, C. Palladium-Catalyzed C−N(sp2) Bond Formation:&#8201;N-Arylation of Aromatic and Unsaturated Nitrogen and the Reductive Elimination Chem-istry of Palladium Azolyl and Methyleneamido Complexes. J. Am. Chem. Soc., 1998, 120, 827-828.
[http://dx.doi.org/10.1021/ja973524g]
[11]
Correa, A.; Bolm, C. Iron-catalyzed N-arylation of nitrogen nucleophiles. Angew. Chem. Int. Ed. Engl., 2007, 46(46), 8862-8865.
[http://dx.doi.org/10.1002/anie.200703299] [PMID: 17943927]
[12]
Altman, R.A.; Shafir, A.; Choi, A.; Lichtor, P.A.; Buchwald, S.L. An improved Cu-based catalyst system for the reactions of alcohols with aryl halides. J. Org. Chem., 2008, 73(1), 284-286.
[http://dx.doi.org/10.1021/jo702024p] [PMID: 18044928]
[13]
Chen, Y-J.; Chen, H-H. 1,1,1-tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod lig-and for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols. Org. Lett., 2006, 8(24), 5609-5612.
[http://dx.doi.org/10.1021/ol062339h] [PMID: 17107084]
[14]
Ma, D.; Cai, Q.N. N-dimethyl glycine-promoted Ullmann coupling reaction of phenols and aryl hal-ides. Org. Lett., 2003, 5(21), 3799-3802.
[http://dx.doi.org/10.1021/ol0350947] [PMID: 14535713]
[15]
Kwong, F.Y.; Klapars, A.; Buchwald, S.L. Copper-catalyzed coupling of alkylamines and aryl io-dides: An efficient system even in an air atmosphere. Org. Lett., 2002, 4(4), 581-584.
[http://dx.doi.org/10.1021/ol0171867] [PMID: 11843596]
[16]
Lipshutz, B.H.; Unger, J.B.; Taft, B.R. Copper-in-charcoal (Cu/C) promoted diaryl ether formation. Org. Lett., 2007, 9(6), 1089-1092.
[http://dx.doi.org/10.1021/ol0700409] [PMID: 17305352]
[17]
Klapars, A.; Antilla, J.C.; Huang, X.; Buchwald, S.L. A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles. J. Am. Chem. Soc., 2001, 123(31), 7727-7729.
[http://dx.doi.org/10.1021/ja016226z] [PMID: 11481007]
[18]
Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. Accelerating effect induced by the structure of α-amino acid in the copper-catalyzed coupling reaction of aryl halides with α-amino acids. Synthesis of benzo-lactam-V8. J. Am. Chem. Soc., 1998, 120, 12459-12467.
[http://dx.doi.org/10.1021/ja981662f]
[19]
Cristau, H.J.; Cellier, P.P.; Spindler, J.F.; Taillefer, M. Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides. Chemistry, 2004, 10(22), 5607-5622.
[http://dx.doi.org/10.1002/chem.200400582] [PMID: 15457520]
[20]
Xu, L.; Zhu, D.; Wu, F.; Wang, R.; Wan, B. Mild and efficient copper-catalyzed N-arylation of alkyl-amines and N-H heterocycles using an oxime-phosphine oxide ligand. Tetrahedron, 2005, 61, 6553-6560.
[http://dx.doi.org/10.1016/j.tet.2005.04.053]
[21]
Xie, Y.X.; Pi, S.F.; Wang, J.; Yin, D.L.; Li, J.H. 2-aminopyrimidine-4,6-diol as an efficient ligand for solvent-free copper-catalyzed N-arylations of imidazoles with aryl and heteroaryl halides. J. Org. Chem., 2006, 71(21), 8324-8327.
[http://dx.doi.org/10.1021/jo061572q] [PMID: 17025338]
[22]
Liu, L.; Frohn, M.; Xi, N.; Dominguez, C.; Hungate, R.; Reider, P.J. A soluble base for the copper-catalyzed imidazole N-arylations with aryl halides. J. Org. Chem., 2005, 70(24), 10135-10138.
[http://dx.doi.org/10.1021/jo051640t] [PMID: 16292856]
[23]
Tang, B.X.; Guo, S.M.; Zhang, M.B.; Li, J.H. N-arylations of nitrogen-containing heterocycles with aryl and heteroaryl halides using a copper (I) oxide nanoparticle/1, 10-phenanthroline catalytic system. Synthesis, 2008, 1707-1716.
[24]
Altman, R.A.; Buchwald, S.L. 4,7-Dimethoxy-1,10-phenanthroline: An excellent ligand for the Cu-catalyzed N-arylation of imidazoles. Org. Lett., 2006, 8(13), 2779-2782.
[http://dx.doi.org/10.1021/ol0608505] [PMID: 16774255]
[25]
Lv, X. Bao, W. A β-keto ester as a novel, efficient, and versatile ligand for copper(I)-catalyzed C-N, C-O, and C-S coupling reactions. J. Org. Chem., 2007, 72(10), 3863-3867.
[http://dx.doi.org/10.1021/jo070443m] [PMID: 17432916]
[26]
Liu, Y.S.; Gu, N.N.; Liu, Y.; Ma, X.W.; Liu, P.; Xie, J.W. 3-(Diphenylphosphino) propanoic Acid: An Efficient Ligand for Cu-Catalyzed N-Arylations of Indoles and Aryl Amines. Asian J. Chem., 2015, 27, 1075-1078.
[http://dx.doi.org/10.14233/ajchem.2015.18258]
[27]
Clark, J.S.K.; Voth, C.N.; Ferguson, M.J.; Stradiotto, M. Evaluating 1, 1′-Bis (phosphino) ferrocene Ancillary Ligand Variants in the Nickel-Catalyzed C-N Cross-Coupling of (Hetero) aryl Chlorides. Organometallics, 2017, 36, 679-686.
[http://dx.doi.org/10.1021/acs.organomet.6b00885]
[28]
Swapna, K.; Murthy, S.N.; Nageswar, Y.V.D. Copper Iodide as a Recyclable Catalyst for Buchwald N-Arylation. Eur. J. Org. Chem., 2010, 34, 6678-6684.
[http://dx.doi.org/10.1002/ejoc.201000964]
[29]
Yang, Q.; Lei, X.; Yin, Z.; Deng, Z.; Peng, Y. Copper-Catalyzed NaBAr4-Based N-Arylation of Amines. Synthesis, 2019, 51, 538-544.
[http://dx.doi.org/10.1055/s-0037-1610251]
[30]
Yu, J-F.; Li, J-J.; Wang, P.; Yu, J.Q. Cu-Mediated Amination of (Hetero)Aryl C-H bonds with NH Azaheterocycles. Angew. Chem. Int. Ed. Engl., 2019, 58(50), 18141-18145.
[http://dx.doi.org/10.1002/anie.201910395] [PMID: 31625662]
[31]
Roch, A.L.; Chan, H.C.; Gagnon, A. Copper-Promoted N-Arylation of the Indole Side Chain of Tryptophan using Triarylbismuthines. Eur. J. Org. Chem., 2020, 2020, 5815-5819.
[http://dx.doi.org/10.1002/ejoc.202000667]
[32]
Zha, G-J.; Ji, W.; Qi, Z-H.; Qiu, W-J.; Li, A-M.; Zhu, D-R.; Jing, S. Microenvironment modulation of cuprous cluster enables inert aryl chlorides activation in single-molecule metallaphotoredox amina-tion. J. Catal., 2022, 405, 313-321.
[http://dx.doi.org/10.1016/j.jcat.2021.12.007]
[33]
Kundu, A.; Kumar, V.V.; Anthony, S.P. Metal-organic frameworks derived CuONPs@C nanocata-lysts for synthesizing optoelectronic triarylamine molecules. Inorg. Chem. Commun., 2021, 123, 108301-108303.
[http://dx.doi.org/10.1016/j.inoche.2020.108301]
[34]
Chan, H-C.; Bueno, B.; Le Roch, A.; Gagnon, A. Copper-Promoted N-Arylation of the Imidazole Side Chain of Protected Histidine by Using Triarylbismuth Reagents. Chemistry, 2021, 27(53), 13330-13336.
[http://dx.doi.org/10.1002/chem.202102186] [PMID: 34357653]
[35]
Börger, C.; Kataeva, O.; Knölker, H-J. Novel approach to biscarbazole alkaloids via Ullmann cou-pling--synthesis of murrastifoline-A and bismurrayafoline-A. Org. Biomol. Chem., 2012, 10(36), 7269-7273.
[http://dx.doi.org/10.1039/c2ob26229k] [PMID: 22875057]
[36]
Oeser, P.; Koudelka, J.; Petrenko, A.; Tobrman, T. Recent Progress concerning the N-. Molecules, 2021, 26(16), 5079-5122.
[http://dx.doi.org/10.3390/molecules26165079] [PMID: 34443667]
[37]
Hisana, K.N.; Afsina, C.M.A.; Anilkumar, G. Copper-catalyzed N-arylation of pyrroles: An overview. New J. Chem., 2021, 45, 17061-17076.
[http://dx.doi.org/10.1039/D1NJ02638K]
[38]
Ananthu, S.; Aneeja, T.; Anilkumar, G. N-arylation of imodazoles: An overview. ChemistrySelect, 2021, 6, 9794-9805.
[http://dx.doi.org/10.1002/slct.202102411]
[39]
Cheng, Y.; Yu, S.; He, Y.; An, G.; Li, G.; Yang, Z. C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by tuning Pd catalytic modes: Pd(i)-Pd(ii) catalysis vs. Pd(ii) catalysis. Chem. Sci. (Camb.), 2021, 12(9), 3216-3225.
[http://dx.doi.org/10.1039/D0SC05409G] [PMID: 34164090]
[40]
Xu, H. Advances on N-Arylation of Indoles by Cross-Coupling Reactions. Mini Rev. Org. Chem., 2009, 6, 367-377.
[http://dx.doi.org/10.2174/157019309789371613]
[41]
Hedidi, M.; Bentabed-Ababsa, G.; Derdour, A.; Roisnel, T.; Dorcet, V.; Chevallier, F.; Picot, L.; Thiéry, V.; Mongin, F. Synthesis of C,N′-linked bis-heterocycles using a deprotometalation-iodination-N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells. Bioorg. Med. Chem., 2014, 22(13), 3498-3507.
[http://dx.doi.org/10.1016/j.bmc.2014.04.028] [PMID: 24831678]
[42]
Chen, Y.; Du, F.; Chen, F.; Zhou, Q.; Chen, G. Methyl-α-D-glucopyranoside as Green Ligand for Se-lective Copper-Catalyzed N-Arylation. Synthesis, 2019, 51, 4590-4600.
[http://dx.doi.org/10.1055/s-0039-1690702]
[43]
Zhou, Q.; Du, F.; Chen, Y.; Fu, Y.; Sun, W.; Wu, Y.; Chen, G. l -(-) -Quebrachitol as a ligand for se-lective copper(0)-catalyzed N-arylation of nitrogen-containing heterocycles. J. Org. Chem., 2019, 84(12), 8160-8167.
[http://dx.doi.org/10.1021/acs.joc.9b00997] [PMID: 31190531]
[44]
Lee, H.S.; Kim, S.H.; Kim, Y.M.; Kim, J.N. An expedient synthesis of indolo[1,2-a]quinolines via Mn(OAc)3-mediated oxidative free radical cyclization and NaI/O2-assisted dealkoxycarbonyla-tion/aerobic oxidation cascade. Tetrahedron, 2010, 51, 5071-5075.
[http://dx.doi.org/10.1016/j.tetlet.2010.07.092]
[45]
Ma, H.; Wu, S.; Sun, Q.; Lei, Z. Oxazolidin-2-one as efficient ligand for the copper-catalyzed N ary-lation of pyrrole, imidazole and indole. Lett. Org. Chem., 2010, 7, 212-218.
[http://dx.doi.org/10.2174/157017810791112496]
[46]
Vaillard, V.A.; Rossi, R.A.; Martín, S.E. Synthesis of pyrrole and indole quinoxalinone and oxazi-none derivatives by intramolecular copper-catalyzed reactions. Org. Biomol. Chem., 2011, 9(13), 4927-4935.
[http://dx.doi.org/10.1039/c1ob05269a] [PMID: 21597621]
[47]
Yang, X.; Xing, H.; Zhang, Y.; Lai, Y.; Zhang, Y.; Jiang, Y.; Ma, D. CuI/8-Hydroxyquinalidine Pro-moted N-Arylation of Indole and Azoles. Chin. J. Chem., 2012, 30, 875-880.
[http://dx.doi.org/10.1002/cjoc.201100433]
[48]
Liu, S.; Zhou, J. Aqueous copper-catalyzed N-arylation of indoles: The surfactant strategy. J. New J. Chem., 2013, 37, 2537-2540.
[http://dx.doi.org/10.1039/c3nj00226h]
[49]
Zhang, B-H.; Shi, L-X.; Liu, S-J.; Guo, R-X. N-arylation of heterocycles promoted by cyclen deriv-atives. J. Heterocycl. Chem., 2014, 52, 1234-1239.
[http://dx.doi.org/10.1002/jhet.2188]
[50]
Chen, H.; Lei, M.; Hu, L. Synthesis of 1-aryl indoles via coupling reaction of indoles and aryl halides catalyzed by CuI/metformin. Tetrahedron, 2014, 70, 5626-5631.
[http://dx.doi.org/10.1016/j.tet.2014.06.080]
[51]
Yadav, D.K.T.; Rajak, S.S.; Bhanage, B.M. N-arylation of indoles with aryl halides using cop-per/glycerol as a mild and highly efficient recyclable catalytic system. Tetrahedron Lett., 2014, 55, 931-935.
[http://dx.doi.org/10.1016/j.tetlet.2013.12.053]
[52]
Patil, P.H.; Nallasivam, J.L.; Fernandes, R.A. Unimolecular 4-Hydroxy Piperidines: New Ligands for Copper Catalyzed N-Arylation. Asian J. Org. Chem., 2015, 4, 552-559.
[http://dx.doi.org/10.1002/ajoc.201500062]
[53]
Taywade, A.; Chavan, S.; Ulhe, A.; Berad, B. Unique CuI-pyridine based ligands catalytic systems for N-arylation of indoles and other heterocycles. Synth. Commun., 2018, 48, 1443-1453.
[http://dx.doi.org/10.1080/00397911.2018.1454474]
[54]
Echeverry-Gonzalez, C.A.; Villamizar, M.C.O.; Kouznetsov, V.V. The remarkable selectivity of the 2-arylquinolinebased acyl hydrazones toward copper salts: Exploration of their catalytic applications in the copper catalysed N-arylation of indole derivatives and C1-alkynylation of tetrahydroisoquino-lines via the A3 reaction. New J. Chem., 2021, 45, 243-250.
[http://dx.doi.org/10.1039/D0NJ04516K]
[55]
Balalaie, S.; Bararjanian, M.; Hosseinzadeh, S.; Rominger, F.; Bijanzadeh, H.R.; Wolf, E. Designing a sequential Ugi/Ullmann type reaction for the synthesis of indolo[1,2-a]quinoxalinones catalyzed by CuI/L-proline. Tetrahedron, 2011, 67, 7294-7300.
[56]
Zhang, L.; Zhao, F.; Zheng, M.; Zhai, Y.; Liu, H. Rapid and selective access to three distinct sets of indole-based heterocycles from a single set of Ugi-adducts under microwave heating. Chem. Commun. (Camb.), 2013, 49(28), 2894-2896.
[http://dx.doi.org/10.1039/c3cc00111c] [PMID: 23451339]
[57]
Ziegler, D.T.; Choi, J.; Muñoz-Molina, J.M.; Bissember, A.C.; Peters, J.C.; Fu, G.C. A versatile ap-proach to Ullmann C-N couplings at room temperature: New families of nucleophiles and electrophiles for photoinduced, copper-catalyzed processes. J. Am. Chem. Soc., 2013, 135(35), 13107-13112.
[http://dx.doi.org/10.1021/ja4060806] [PMID: 23968565]
[58]
Modha, S.G.; Greaney, M.F. Atom-economical transformation of diaryliodonium salts: Tandem C-H and N-H arylation of indoles. J. Am. Chem. Soc., 2015, 137(4), 1416-1419.
[http://dx.doi.org/10.1021/ja5124754] [PMID: 25588092]
[59]
Wang, Y.; Zhang, Y.; Yang, B.; Zhang, A.; Yao, Q.N. -(1-Oxy-2-picolyl)oxalamic acids as a new type of O,O-ligands for the Cu-catalyzed N-arylation of azoles with aryl halides in water or organic sol-vent. Org. Biomol. Chem., 2015, 13(13), 4101-4114.
[http://dx.doi.org/10.1039/C5OB00045A] [PMID: 25740426]
[60]
Ge, X.; Zhang, S.; Chen, X.; Quian, C. A designed bi-functional sugar-based surfactant: Micellar ca-talysis for C-X coupling reaction in water. Green Chem., 2019, 21, 2771-2776.
[http://dx.doi.org/10.1039/C9GC00964G]
[61]
Zhou, G.; Chen, W.; Zhang, S.; Liu, X.; Yang, Z.; Ge, X.; Fan, H-J. A newly designed carbohydrate-derived alkylamine promotes ullmann type C-N coupling catalyzed by copper in water. Synlett, 2019, 30, 193-198.
[http://dx.doi.org/10.1055/s-0037-1611695]
[62]
Vaidya, G.N.; Khan, A.; Verma, H.; Kumar, S.; Kumar, D. Structure Ligation relationship of amino acids for the amination cross-coupling reactions. J. Org. Chem., 2019, 84(5), 3004-3010.
[http://dx.doi.org/10.1021/acs.joc.8b03214] [PMID: 30734563]
[63]
Malavade, V.; Patil, M. Scope, Kinetics and Mechanism of “On Water” Cu Catalysis in the C - N Cross Coupling Reactions of Indole derivatives. Eur. J. Org. Chem., 2020, 2020, 561-569.
[http://dx.doi.org/10.1002/ejoc.201901542]
[64]
Lee, J.; Choi, J.H.; Shin, S.; Heo, J-N.; Lim, H.J. N-arylation of sterically hindered NH-nucleophiles: Copper-mediated syntheses of diverse N-arylindole-2-carboxylates. Synthesis, 2015, 47, 3301-3308.
[http://dx.doi.org/10.1055/s-0035-1560065]
[65]
Li, X.; Yang, D.; Jiang, Y.; Fu, H. Efficient copper-catalyzed N-arylations of nitrogen-containing het-erocycles and aliphatic amines in water. Green Chem., 2010, 12, 1097-1105.
[http://dx.doi.org/10.1039/c002172e]
[66]
Yang, K.; Qiu, Y.; Li, Z.; Wang, Z.; Jiang, S. Ligands for copper-catalyzed C-N bond forming reac-tions with 1 mol% CuBr as catalyst. J. Org. Chem., 2011, 76(9), 3151-3159.
[http://dx.doi.org/10.1021/jo1026035] [PMID: 21425835]
[67]
Engel-Andreasen, J.; Shimpukade, B.; Ulven, T. Selective copper catalysed aromatic N-arylation in water. Green Chem., 2013, 15, 336-340.
[http://dx.doi.org/10.1039/C2GC36589H]
[68]
Bollenbach, M.; Aquino, P.G.V.; de Araújo-Júnior, J.X.; Bourguignon, J-J.; Bihel, F.; Salomé, C.; Wagner, P.; Schmitt, M. Efficient and mild ullmann-type N-arylation of amides, carbamates, and az-oles in water. Chemistry, 2017, 23(55), 13676-13683.
[http://dx.doi.org/10.1002/chem.201700832] [PMID: 28696045]
[69]
Abe, T.; Takahashi, Y.; Matsubara, Y.; Yamada, K. An Ullmann N-arylation/2-amidation cascade by self-relay copper catalysis: One-pot synthesis of indolo[1,2 a]quinazolinones. Org. Chem. Front., 2017, 4, 2124-2127.
[http://dx.doi.org/10.1039/C7QO00549K]
[70]
Yuan, C. Zhao, Y.; Zheng, L. α-D-galacturonic acid as natural ligand for selective copper-catalyzed N-arylation of N-containing heterocycles. Synlett, 2019, 30, 2173-2180.
[http://dx.doi.org/10.1055/s-0039-1690226]
[71]
Yong, F-F.; Teo, Y-C.; Tay, S-H.; Tan, B.Y-H.; Lim, K-H. A ligand-free copper(I) oxide catalyzed strategy for the N-arylation of azoles in water. Tetrahedron Lett., 2011, 52, 1161-1164.
[http://dx.doi.org/10.1016/j.tetlet.2011.01.005]
[72]
Hedidi, M.; Erb, W.; Bentabed-Ababsa, G.; Chevallier, F.; Picot, L.; Thiéry, V.; Bach, S.; Ruchaud, S.; Roisnel, T.; Dorcet, Y. Synthesis of N-pyridyl azoles using a deprotometalation-iodolysis- N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells. Tetrahedron, 2016, 72, 6467-6476.
[http://dx.doi.org/10.1016/j.tet.2016.08.056]
[73]
Zhang, Y.; Hu, Z-Y.; Li, X-C.; Guo, X-X. Copper-Catalyzed Decarboxylative N-Arylation of Indole-2-carboxylic Acids. Synthesis, 2019, 51, 1803-1808.
[http://dx.doi.org/10.1055/s-0037-1611946]
[74]
Wei, J.J.; Song, W.B.; Zhu, Y.F.; Wei, B.L.; Xuan, L.J.N. N-dimethyl-D-glucosamine as an efficient ligand for copper-catalyzed Ullmann-type coupling of NH heterocycles with aryl halides. Tetrahedron, 2018, 74, 19-27.
[http://dx.doi.org/10.1016/j.tet.2017.11.027]
[75]
Damkaci, F.; Alawaed, A.; Vik, E. N-Picolinamides as ligands for Ullmann-type C-N coupling reac-tions. Tetrahedron Lett., 2016, 57, 2197-2200.
[http://dx.doi.org/10.1016/j.tetlet.2016.04.017]
[76]
Liu, L.; Wu, F.; Liu, Y.; Xie, J.; Dai, B.; Zhou, Z. Copper-catalysed N-arylation of pyrrole with aryl iodides under ligand-free Conditions. J. Chem. Res., 2014, 38, 180-182.
[http://dx.doi.org/10.3184/174751914X13922969308054]
[77]
Yan, N-N.; Wu, F-T.; Zhang, Z. Wei, Q.-B.; Liu, P.; Xie, J.-W.; Dai, B. Efficient Copper Catalyzed C- N Coupling Reaction in Water by Using 2‐ Hydroxybenzohydrazides as Ligands. Asian J. Org. Chem., 2014, 3, 1159-1162.
[http://dx.doi.org/10.1002/ajoc.201402136]
[78]
Xu, Z-L.; Li, H-X.; Ren, Z-G.; Du, W-Y.; Xu, W-C.; Lang, J-P. Cu(OAc)2.H2O-catalyzed N-arylation of nitrogen-containing heterocycle. Tetrahedron, 2011, 67, 5282-5288.
[http://dx.doi.org/10.1016/j.tet.2011.05.025]
[79]
Farahat, A.A.; Boykin, D.W. Copper (I) 3-methylsalicylate, an efficient catalyst for N-arylation of heterocycles under moderate reaction conditions. Tetrahedron Lett., 2014, 55, 3049-3051.
[http://dx.doi.org/10.1016/j.tetlet.2014.03.117]
[80]
Németh, J.; Debreczeni, N.; Gresits, I.; Bálint, M.; Hell, Z. An efficient heterogeneous catalytic meth-od for the N-arylation of pyrrole and other N-heterocycles. Catal. Lett., 2015, 145, 1113-1119.
[http://dx.doi.org/10.1007/s10562-015-1523-6]
[81]
Teo, Y-C.; Yong, F-F.; Lim, G.S. A manganese/copper bimetallic catalyst for C-N coupling reactions under mild conditions in water. Tetrahedron Lett., 2011, 52, 7171-7174.
[http://dx.doi.org/10.1016/j.tetlet.2011.10.128]
[82]
Ghosh, T.; Maity, P.; Ranu, B.C. Cobalt-copper catalyzed C(sp2) - N cross coupling of amides or ni-trogenated heterocycles with styrenyl or aryl halides. ChemistrySelect, 2018, 3, 4406-4412.
[http://dx.doi.org/10.1002/slct.201800575]
[83]
Suramwar, N.V.; Thakare, S.R.; Karade, N.N.; Khaty, N.T. Green synthesis of predominant (1 1 1) facet CuO nanoparticles: Heterogeneous and recyclable catalyst for N-arylation of indoles. J. Mol. Catal., 2012, 359, 28-34.
[http://dx.doi.org/10.1016/j.molcata.2012.03.017]
[84]
Nasrollahzadeh, M.; Sajadi, S.M.; Rostami-Vartooni, A.; Hussin, S.M. Green synthesis of CuO nano-particles using aqueous extract of Thymus vulgaris L. leaves and their catalytic performance for N-arylation of indoles and amines. J. Colloid Interface Sci., 2016, 466, 113-119.
[http://dx.doi.org/10.1016/j.jcis.2015.12.018] [PMID: 26707778]
[85]
Veisi, H.; Hemmati, S.; Javaheri, H. N-Arylation of indole and aniline by a green synthesized CuO nanoparticles mediated by Thymbra spicata leaves extract as a recyclable and heterogeneous nano-catalyst. Tetrahedron, 2017, 58, 3155-3159.
[http://dx.doi.org/10.1016/j.tetlet.2017.06.086]
[86]
Khalil, A.; Fihri, A.; Jouiad, M.; Hashaikeh, R. Electrospun copper oxide nanoparticles as an efficient heterogeneous catalyst for N-arylation of indole. Tetrahedron, 2014, 55, 5973-5975.
[http://dx.doi.org/10.1016/j.tetlet.2014.08.120]
[87]
Panda, N.; Jena, A.K.; Mohapatra, S.; Rout, S.R. Copper ferrite nanoparticle-mediated N-arylation of heterocycles: A ligand-free reaction. Tetrahedron Lett., 2011, 52, 1924-1927.
[http://dx.doi.org/10.1016/j.tetlet.2011.02.050]
[88]
Nakhate, A.V.; Yadav, G.D. Hydrothermal Synthesis of CuFe2O4 Magnetic Nanoparticles as Active and Robust Catalyst for N-arylation of Indole and Imidazole with Aryl Halide. ChemistrySelect, 2017, 2, 2395-2405.
[http://dx.doi.org/10.1002/slct.201601846]
[89]
Nakhate, A.V.; Yadav, G.D. Solvothermal synthesis of CuFe2O4@rGO: efficient catalyst for C-O cross coupling and N-arylation reaction under ligand-free condition. ChemistrySelec., 2017, 2, 7150-7159.
[http://dx.doi.org/10.1002/slct.201700556]
[90]
Elhampour, A.; Nemati, F.; Kaveh, M. Cu2O/Nano-CuFe2O4: An efficient and magnetically recovera-ble catalyst for the ligand-free N-arylation of amines and nitrogen heterocycles with aryl halides. Chem. Lett., 2016, 45, 223-225.
[http://dx.doi.org/10.1246/cl.151097]
[91]
Talukdar, D.; Das, G.; Thakur, S.; Karak, N.; Thakur, A.J. Copper nanoparticles decorated Organical-ly Modifed Montmorillonite (OMMT): An efficient catalyst for the N-arylation of indoles and similar heterocycles. Catal. Commun., 2015, 59, 238-243.
[http://dx.doi.org/10.1016/j.catcom.2014.10.030]
[92]
Nandi, D.; Siwal, S.; Mallick, K. Carbon nitride supported copper nanoparticles: A heterogeneous catalyst for the N-arylation of hetero-aromatic compounds. New J. Chem., 2017, 41, 3082-3088.
[http://dx.doi.org/10.1039/C6NJ03584A]
[93]
Esmaeilpour, M.; Sardarian, A.R.; Firouzabadi, H. Dendrimer‐encapsulated Cu(II) nanoparticles im-mobilized on superparamagnetic Fe3O4@SiO2 nanoparticles as a novel recyclable catalyst for N‐arylation of nitrogen heterocycles and green synthesis of 5‐substituted 1H‐tetrazoles. Appl. Organomet. Chem., 2017, 32, 1-16.
[94]
Hemmati, S.; Kamangar, S.A.; Yousefi, M.; Salehi, M.H.; Hekmati, M. Cu (I)-anchored polyvinyl al-cohol coated-magnetic nanoparticles as heterogeneous nanocatalyst in Ullmann&#8208;type C-N coupling re-actions. Appl. Organomet. Chem., 2020, 34, e5611.
[http://dx.doi.org/10.1002/aoc.5611]
[95]
Sardarian, A.R.; Kazemnejadi, M.; Esmaeilpour, M. 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. Appl. Organomet. Chem., 2021, 35, e6051.
[http://dx.doi.org/10.1002/aoc.6051]
[96]
Lim, J.; Kim, J.D.; Choi, H.C.; Lee, S. CNT-CuO catalyzed C-N bond formation for N-arylation of 2-phenylindoles. J. Organomet. Chem., 2019, 902, 120970.
[http://dx.doi.org/10.1016/j.jorganchem.2019.120970]
[97]
Pai, G.; Chattopadhyay, A.P. Ligand-free copper nanoparticle promoted N-arylation of azoles with aryl and heteroaryl iodides. Tetrahedron Lett., 2014, 55, 941-944.
[http://dx.doi.org/10.1016/j.tetlet.2013.12.065]
[98]
Amadine, O.; Maati, H.; Abdelouhadi, K.; Fihri, A.; Kazzouli, S.E.; Len, C.; Bouari, A.E.; Solhy, A. Ceria-supported copper nanoparticles: A highly efficient and recyclable catalyst for N-arylation of in-dole. J. Mol. Catal., 2014, 395, 409-419.
[http://dx.doi.org/10.1016/j.molcata.2014.08.009]
[99]
Veisi, H.; Metghalchi, Y.; Hekmati, M.; Samadzadeh, S. CuI heterogenized on thiosemicarbazide modified‐multi walled carbon nanotubes (thiosemicarbazide‐ MWCNTs‐CuI): Novel heterogeneous and reusable nanocatalyst in the C-N Ullmann coupling reactions. Appl. Organomet. Chem., 2016, 31, 1-7.
[100]
Veisi, H.; Ahmadian, H.; Mirshokraie, S.A.; Didehban, K.; Zangeneh, M.M. CuCl2 heterogenized on metformine-modified polystyrene resin as an antibacterial agent and recyclable nanocatalyst for Ullmann‐type C‐N coupling reactions. Appl. Organomet. Chem., 2019, 33, 1-8.
[http://dx.doi.org/10.1002/aoc.4737]
[101]
Xiao, R.; Zhao, H.; Cai, M. MCM-41-immobilized bidentate nitrogen copper (I) complex: A highly efficient and recyclable catalyst for Buchwald N-arylation of indoles. Tetrahedron, 2013, 69, 5444-5450.
[http://dx.doi.org/10.1016/j.tet.2013.04.106]
[102]
Balaswamy, K.; Pullaiah, P.C.; Rao, M.M. A reusable polystyrene-supported copper (II) catalytic system for N-arylation of indoles and Sonogashira coupling reactions in water. Appl. Catal. A Gen., 2014, 483, 110-115.
[http://dx.doi.org/10.1016/j.apcata.2014.07.001]
[103]
Hosseinzadeh, R.; Aghili, N.; Tajbakhsh, M. SBA-15 immobilized phenanthroline-copper (I) com-plex as a recyclable efficient catalyst for N-arylation of amides and N-H heterocycles with aryl hal-ides. Catal. Lett., 2015, 146, 193-203.
[http://dx.doi.org/10.1007/s10562-015-1622-4]
[104]
Ge, X.; Chen, X.; Qian, C.; Zhou, S. Efficient Ullmann C-N coupling catalyzed by a recoverable oli-gose-supported copper complex. RSC Advances, 2016, 6, 58898-58906.
[http://dx.doi.org/10.1039/C6RA13536F]
[105]
Yadav, K.K.; Narang, U.; Bhattacharya, S.; Chauhan, S.M.S. CopperII phthalocyanine as an efficient and reusable catalyst for the N-arylation of nitrogen containing heterocycles. Tetrahedron Lett., 2017, 58, 3044-3048.
[http://dx.doi.org/10.1016/j.tetlet.2017.06.067]
[106]
Sharghi, H.; Aberi, M.; Shiri, P. Highly reusable support-free copper(II) complex of para-hydroxysubstituted salen: Novel, efficient and versatile catalyst for C-N bond forming reactions. Appl. Organomet. Chem., 2017, 31, e3761.
[http://dx.doi.org/10.1002/aoc.3761]
[107]
Sharghi, H.; Sepehri, S.; Aberi, M. Cu(II) complex of pyridine-based polydentate as a novel, effi-cient, and highly reusable catalyst in C-N bond-forming reaction. Mol. Divers., 2017, 21(4), 855-864.
[http://dx.doi.org/10.1007/s11030-017-9759-2] [PMID: 28653129]
[108]
Zou, Y.; Lin, H.; Maggard, P.A.; Deiters, A. Efficacy of C-N coupling Reactions with a new multi-nuclear copper complex catalyst and its dissociation into mononuclear species. Eur. J. Org. Chem., 2011, 2011, 4154-4159.
[http://dx.doi.org/10.1002/ejoc.201100399]
[109]
Heidarizadeh, F.; Majdi-nasab, A. A green, homogeneous and reusable surfactant/copper based ionic liquid for the N-arylation of indoles, pyrazoles and imidazoles. Tetrahedron, 2015, 56, 6360-6363.
[http://dx.doi.org/10.1016/j.tetlet.2015.09.128]
[110]
Sharghi, H. Saei, A.A.; Aberi, M. N‐arylation of nitrogen-containing heterocycles with Cu (II) complex of 4‐(2, 2′: 6′, 2 “‐terpyridin‐4′‐yl) toluene as a versatile and efficient catalyst. ChemistrySelect, 2019, 4, 13228-13234.
[http://dx.doi.org/10.1002/slct.201903075]
[111]
Kumari, S.; Ratnam, A.; Mawai, K.; Chaudhary, V.K.; Mohanty, A.; Ghosh, K. Cu(I) based cata-lysts derived from bidentate ligands and studies on effect of substituents for N-arylation of benzim-idazoles and indoles. New J. Chem., 2020, 44, 19591-19597.
[http://dx.doi.org/10.1039/D0NJ02568B]
[112]
Li, Z.; Meng, F.; Zhang, J.; Xie, J.; Dai, B. Efficient and recyclable copper-based MOF-catalyzed N-arylation of N-containing heterocycles with aryliodides. Org. Biomol. Chem., 2016, 14(46), 10861-10865.
[http://dx.doi.org/10.1039/C6OB02068B] [PMID: 27808320]
[113]
Ma, P.; Meng, F.; Wang, N.; Zhang, J.; Xie, J.; Dai, B. Heterogeneous amorphous Cu-MOF-74 cata-lyst for C-N coupling reaction. ChemistrySelect, 2018, 3, 10694-10700.
[http://dx.doi.org/10.1002/slct.201802837]
[114]
Bagheri, F.H.; Khabazzadeh, H.; Fayazi, M. Copper-catalyzed N-arylation of bis(indolyl)methanes: The first approach for the synthesis of unsymmetrical N-aryl bis(indolyl)methanes by C-N cross-coupling reaction. C. R. Chim., 2021, 24, 305-317.

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