Recent Advances in N-Arylation of Heterocycles in the Past Decade

Xun      Yang; Haiyan      Li; Quan      Jiang; Zhiguo      Lei; Yuxuan      Xiao; Jialing      Liu; Wengui      Duan; Lin      Yu
doi:10.2174/0113852728320325240710053300
Note! Please note that this article is currently in the "Article in Press" stage and is not the final "Version of record". While it has been accepted, copy-edited, and formatted, however, it is still undergoing proofreading and corrections by the authors. Therefore, the text may still change before the final publication. Although "Articles in Press" may not have all bibliographic details available, the DOI and the year of online publication can still be used to cite them. The article title, DOI, publication year, and author(s) should all be included in the citation format. Once the final "Version of record" becomes available the "Article in Press" will be replaced by that.
Abstract

N-arylated heterocycles are a significant class of core scaffolds in medicinal chemistry, materials science, and agrochemistry, highlighting their importance in various fields. The development of innovative methodologies for synthesizing these fundamental structures has been a central focus in organic synthesis. Over the past few decades, numerous approaches have been established to synthesize N-aryl heterocycles efficiently. Among these methods, the direct N-arylation of N-H heterocycles stands out as one of the most straightforward and robust strategies for accessing N-arylated heterocycles. This review provides a comprehensive review of the recent advances in the synthesis of N-arylated heterocycles, encompassing the relevant literature from the past decade. The review summarizes the N-arylation of N-H heterocycles using various catalytic systems, including palladium, nickel, copper, visible light-induced metal-catalyzed, and metal-free catalyzed methodologies. These advances highlighted the continuous evolution and optimization of synthetic strategies to create diverse and complex N-arylated heterocycles, which are pivotal for furthering research and development in multiple scientific domains.
[1]
Karrouchi, K.; Radi, S.; Ramli, Y.; Taoufik, J.; Mabkhot, Y.N.; Al-aizari, F.A.; Ansar, M. Synthesis and pharmacological activities of pyrazole derivatives: a review. Molecules,  2018, 23(1), 134.
 [http://dx.doi.org/10.3390/molecules23010134] [PMID:  29329257]

[2]
Tripathi, G.; Singh, A.K.; Kumar, A. Arylpyrazoles: Heterocyclic scaffold of immense therapeutic application. Curr. Org. Chem.,  2020, 24(14), 1555-1581.
 [http://dx.doi.org/10.2174/1570179417999200628035645]

[3]
Mermer, A.; Keles, T.; Sirin, Y. Recent studies of nitrogen containing heterocyclic compounds as novel antiviral agents: A review. Bioorg. Chem.,  2021, 114, 105076.
 [http://dx.doi.org/10.1016/j.bioorg.2021.105076] [PMID:  34157555]

[4]
Bansal, Y.; Minhas, R.; Singhal, A.; Arora, R.K.; Bansal, G. Benzimidazole: a multifacted nucelus for anticancer agents. Curr. Org. Chem.,  2021, 25(6), 669-694.
 [http://dx.doi.org/10.2174/1385272825666210208141107]

[5]
Hashem, H.E.; El Bakri, Y. An overview on novel synthetic approaches and medicinal applications of benzimidazole compounds. Arab. J. Chem.,  2021, 14(11), 103418.
 [http://dx.doi.org/10.1016/j.arabjc.2021.103418]

[6]
Mir, R.H. Mohi-ud-din, R.; Wani, T.U.; Dar, M.O.; Shah, A.J.; Lone, B.; Pooja, C.; Masoodi, M.H. Indole: A privileged heterocyclic moiety in the management of cancer. Curr. Org. Chem.,  2021, 25(6), 724-736.
 [http://dx.doi.org/10.2174/1385272825666210208142108]

[7]
Rani, M.; Utreja, D.; Sharma, S. Role of indole derivatives in agrochemistry: synthesis and future insights. Curr. Org. Chem.,  2022, 26(7), 651-678.
 [http://dx.doi.org/10.2174/1385272826666220426103835]

[8]
Mondal, D.; Kalar, P.L.; Kori, S.; Gayen, S.; Das, K. Recent developments on synthesis of indole derivatives through green approaches and their pharmaceutical applications. Curr. Org. Chem.,  2020, 24(22), 2665-2693.
 [http://dx.doi.org/10.2174/1385272824999201111203812]

[9]
Allen, L.A.T.; Natho, P. Trends in carbazole synthesis – an update (2013–2023). Org. Biomol. Chem.,  2023, 21(45), 8956-8974.
 [http://dx.doi.org/10.1039/D3OB01605F] [PMID:  37906471]

[10]
Hou, W.; Dai, W.; Huang, H.; Liu, S.L.; Liu, J.; Huang, L.J.; Huang, X.H.; Zeng, J.L.; Gan, Z.W.; Zhang, Z.Y.; Lan, J.X. Pharmacological activity and mechanism of pyrazines. Eur. J. Med. Chem.,  2023, 258, 115544.
 [http://dx.doi.org/10.1016/j.ejmech.2023.115544] [PMID:  37300915]

[11]
Singh, S.; Tahlan, S.; Singh, K.; Verma, P.K. Synthetic update on antimicrobial potential of novel pyrazole derivatives: a review. Curr. Org. Chem.,  2024, 28(5), 325-345.
 [http://dx.doi.org/10.2174/0113852728292094240216045039]

[12]
Boyd, E.M.; Sperry, J. Total synthesis of (-)-aspergilazine A. Org. Lett.,  2014, 16(19), 5056-5059.
 [http://dx.doi.org/10.1021/ol5024097] [PMID:  25248025]

[13]
Wyche, T.P.; Ruzzini, A.C.; Schwab, L.; Currie, C.R.; Clardy, J. Tryptorubin a: A polycyclic peptide from a fungus-derived streptomycete. J. Am. Chem. Soc.,  2017, 139(37), 12899-12902.
 [http://dx.doi.org/10.1021/jacs.7b06176] [PMID:  28853867]

[14]
Tasler, S.; Bringmann, G. Biarylic biscarbazole alkaloids: occurrence, stereochemistry, synthesis, and bioactivity. Chem. Rec.,  2002, 2(2), 113-126.
 [http://dx.doi.org/10.1002/tcr.10014] [PMID:  12001210]

[15]
Ahmad, S.; Alam, O.; Naim, M.J.; Shaquiquzzaman, M.; Alam, M.M.; Iqbal, M. Pyrrole: An insight into recent pharmacological advances with structure activity relationship. Eur. J. Med. Chem.,  2018, 157, 527-561.
 [http://dx.doi.org/10.1016/j.ejmech.2018.08.002] [PMID:  30119011]

[16]
Li Petri, G.; Spanò, V.; Spatola, R.; Holl, R.; Raimondi, M.V.; Barraja, P.; Montalbano, A. Bioactive pyrrole-based compounds with target selectivity. Eur. J. Med. Chem.,  2020, 208, 112783.
 [http://dx.doi.org/10.1016/j.ejmech.2020.112783] [PMID:  32916311]

[17]
Kulkarni, A.; Soni, I.; Kelkar, D.S.; Dharmaraja, A.T.; Sankar, R.K.; Beniwal, G.; Rajendran, A.; Tamhankar, S.; Chopra, S.; Kamat, S.S.; Chakrapani, H. Chemoproteomics of an indole-based quinone epoxide identifies druggable vulnerabilities in vancomycin-resistant Staphylococcus aureus. J. Med. Chem.,  2019, 62(14), 6785-6795.
 [http://dx.doi.org/10.1021/acs.jmedchem.9b00774] [PMID:  31241934]

[18]
Puxeddu, M.; Shen, H.; Bai, R.; Coluccia, A.; Bufano, M.; Nalli, M.; Sebastiani, J.; Brancaccio, D.; Da Pozzo, E.; Tremolanti, C.; Martini, C.; Orlando, V.; Biagioni, S.; Sinicropi, M.S.; Ceramella, J.; Iacopetta, D.; Coluccia, A.M.L.; Hamel, E.; Liu, T.; Silvestri, R.; La Regina, G. Discovery of pyrrole derivatives for the treatment of glioblastoma and chronic myeloid leukemia. Eur. J. Med. Chem.,  2021, 221, 113532.
 [http://dx.doi.org/10.1016/j.ejmech.2021.113532] [PMID:  34052717]

[19]
Andersen, K.; Liljefors, T.; Hyttel, J.; Perregaard, J. Serotonin 5-HT2 receptor, dopamine D2 receptor, and α 1 adrenoceptor antagonists. Conformationally flexible analogues of the atypical antipsychotic sertindole. J. Med. Chem.,  1996, 39(19), 3723-3738.
 [http://dx.doi.org/10.1021/jm960159f] [PMID:  8809161]

[20]
Xu, H.; Liu, W.Q.; Fan, L.L.; Chen, Y.; Yang, L.M.; Lv, L.; Zheng, Y.T. Synthesis and HIV-1 integrase inhibition activity of some N-arylindoles. Chem. Pharm. Bull. (Tokyo),  2008, 56(5), 720-722.
 [http://dx.doi.org/10.1248/cpb.56.720] [PMID:  18451566]

[21]
Tao, Y.; Yang, C.; Qin, J. Organic host materials for phosphorescent organic light-emitting diodes. Chem. Soc. Rev.,  2011, 40(5), 2943-2970.
 [http://dx.doi.org/10.1039/c0cs00160k] [PMID:  21369622]

[22]
Wu, Y.; Li, Y.; Gardner, S.; Ong, B.S. Indolo[3,2-b]carbazole-based thin-film transistors with high mobility and stability. J. Am. Chem. Soc.,  2005, 127(2), 614-618.
 [http://dx.doi.org/10.1021/ja0456149] [PMID:  15643885]

[23]
Shang, T.Y.; Lu, L.H.; Cao, Z.; Liu, Y.; He, W.M.; Yu, B. Recent advances of 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) in photocatalytic transformations. Chem. Commun. (Camb.),  2019, 55(38), 5408-5419.
 [http://dx.doi.org/10.1039/C9CC01047E] [PMID:  31020957]

[24]
Uoyama, H.; Goushi, K.; Shizu, K.; Nomura, H.; Adachi, C. Highly efficient organic light-emitting diodes from delayed fluorescence. Nature,  2012, 492(7428), 234-238.
 [http://dx.doi.org/10.1038/nature11687] [PMID:  23235877]

[25]
Huang, Z.; Chen, Z.; Jiang, Y.; Li, N.; Yang, S.; Wang, G.; Pan, X. Metal-free hydrosilylation polymerization by merging photoredox and hydrogen atom transfer catalysis. J. Am. Chem. Soc.,  2021, 143(45), 19167-19177.
 [http://dx.doi.org/10.1021/jacs.1c09263] [PMID:  34738793]

[26]
Kamboj, M.; Bajpai, S.; Banik, B.K. Microwave-induced reactions for pyrrole synthesis. Curr. Org. Chem.,  2023, 27(7), 559-567.
 [http://dx.doi.org/10.2174/1385272827666230508124450]

[27]
Beifuss, U.; Moustafa, A.; Malakar, C.; Aljaar, N.; Merisor, E.; Conrad, J. Microwave-assisted molybdenum-catalyzed reductive cyclization of o-Nitrobenzylidene amines to 2-aryl-2H-Indazoles. Synlett,  2013, 24(12), 1573-1577.
 [http://dx.doi.org/10.1055/s-0033-1339195]

[28]
Singh, D.; Devi, N.; Kumar, V.; Malakar, C.C.; Mehra, S.; Rawal, R.K.; Kaith, B.S.; Singh, V. Metal-free 1,3-dipolar cycloaddition approach towards the regioselective synthesis of β-carboline and isoxazole based molecular hybrids. RSC Advances,  2016, 6(91), 88066-88076.
 [http://dx.doi.org/10.1039/C6RA15875G]

[29]
Singh, D.; Kumar, V.; Devi, N.; Malakar, C.C.; Shankar, R.; Singh, V. Metal–free decarboxylative amination: an alternative approach towards regioselective synthesis of β-carboline N-fused imidazoles. Adv. Synth. Catal.,  2017, 359(7), 1213-1226.
 [http://dx.doi.org/10.1002/adsc.201600970]

[30]
Gujjarappa, R.; Vodnala, N.; Kabi, A.; Kaldhi, D.; Kumar, M.; Beifuss, U.; Malakar, C. Efficient syntheses of diverse N-heterocycles: The molybdenum (vi)-catalyzed reductive cyclization of nitroarenes using pinacol as a	deoxygenating agent. SynOpen, 2018, 2(2), 0138-0144.
 [http://dx.doi.org/10.1055/s-0036-1591572]

[31]
Iqbal, S.; Rasheed, H.; Awan, R.J.; Awan, R.J.; Mukhtar, A.; Moloney, M.G. Recent advances in the synthesis of pyrroles. Curr. Org. Chem.,  2020, 24(11), 1196-1229.
 [http://dx.doi.org/10.2174/1385272824999200528125651]

[32]
Chebieb, A.; Kim, Y.G.; Cha, J.K. Synthesis of Indoles from o-Haloanilines. J. Org. Chem.,  2023, 88(14), 10164-10170.
 [http://dx.doi.org/10.1021/acs.joc.3c01047] [PMID:  37410990]

[33]
Kumar, S.; Kumar, R.; Malakar, C.C.; Singh, V. Copper catalysed regioselective synthesis of pyrimidine substituted Indolizino[8,7-b]indole derivatives via cascade A3 annulation. Tetrahedron,  2023, 142, 133547.
 [http://dx.doi.org/10.1016/j.tet.2023.133547]

[34]
Patel, C.K.; Gujjarappa, R.; Kant, K.; Ghanta, S.; Singh, V.; Kabi, A.K.; Al-Zaqri, N.; Malakar, C.C. Copper-catalyzed c(sp3)− functionalization and annulation of 2-bromoaryl oximes with active methylene compounds towards synthesis of isoquinoline N-oxides. Adv. Synth. Catal.,  2023, 365(13), 2203-2210.
 [http://dx.doi.org/10.1002/adsc.202300217]

[35]
Singh, L.S.; Kant, K.; Banerjee, S.; Sengupta, R.; AlObaid, A.A.; Pal, M.; Dutta, S.; Aljaar, N.; Malakar, C.C. The γ-valerolactone (GVL) as innoxious reaction media for the synthesis of 2-aryl-2H-indazoles via C-N and N-N bond formation under Cu(I)-catalyzed ligand and base free conditions. Polycyl. Arom. Comp,  2023, 2023, 1-12.
 [http://dx.doi.org/10.1080/10406638.2023.2257846]

[36]
Singh, D.; Sharma, S.; Thakur, R.K. Vaishali; Nain, S.; Jyoti; Malakar, C.C.; Singh, V. Cu-catalysed diversity-oriented synthesis of isoxazole and imidazo[1,2-a]azine conjugates. Tetrahedron,  2024, 152, 133809.
 [http://dx.doi.org/10.1016/j.tet.2023.133809]

[37]
He, L.; Xu, Y. Palladium-catalyzed synthesis of carbazoles by perester. Adv. Synth. Catal.,  2022, 364(14), 2352-2357.
 [http://dx.doi.org/10.1002/adsc.202200419]

[38]
Points, G.L., III; Beaudry, C.M. Regioselective synthesis of substituted carbazoles, bicarbazoles, and clausine c. Org. Lett.,  2021, 23(17), 6882-6885.
 [http://dx.doi.org/10.1021/acs.orglett.1c02449] [PMID:  34424701]

[39]
Lintott, M.; Perry, A. Straightforward synthesis of N -arylindoles via one-pot Fischer indolisation–indole N -arylation. RSC Advances,  2023, 13(23), 15993-15997.
 [http://dx.doi.org/10.1039/D3RA02658B] [PMID:  37250219]

[40]
Hieu, T.T.; Dung, V.C.; Chung, N.T.; Duc, D.X. Recent achievement in the synthesis of imidazoles. Curr. Org. Chem.,  2023, 27(16), 1398-1446.
 [http://dx.doi.org/10.2174/0113852728259414231010050749]

[41]
Roughley, S.D.; Jordan, A.M. The medicinal chemist’s toolbox: an analysis of reactions used in the pursuit of drug candidates. J. Med. Chem.,  2011, 54(10), 3451-3479.
 [http://dx.doi.org/10.1021/jm200187y] [PMID:  21504168]

[42]
Dorel, R.; Grugel, C.P.; Haydl, A.M. The Buchwald–Hartwig amination after 25 years. Angew. Chem. Int. Ed.,  2019, 58(48), 17118-17129.
 [http://dx.doi.org/10.1002/anie.201904795] [PMID:  31166642]

[43]
Forero-Cortés, P.A.; Haydl, A.M. The 25th anniversary of the Buchwald–Hartwig amination: development, applications, and outlook. Org. Process Res. Dev.,  2019, 23(8), 1478-1483.
 [http://dx.doi.org/10.1021/acs.oprd.9b00161]

[44]
Heravi, M.M.; Kheilkordi, Z.; Zadsirjan, V.; Heydari, M.; Malmir, M. Buchwald-Hartwig reaction: An overview. J. Organomet. Chem.,  2018, 861, 17-104.
 [http://dx.doi.org/10.1016/j.jorganchem.2018.02.023]

[45]
Kunz, K.; Scholz, U.; Ganzer, D. Renaissance of Ullmann and goldberg reactions - progress in copper catalyzed C-N-, C-O- and C-S-coupling. Synlett,  2003, 2003(15), 2428-2439.
 [http://dx.doi.org/10.1055/s-2003-42473]

[46]
Sambiagio, C.; Marsden, S.P.; Blacker, A.J.; McGowan, P.C. Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development. Chem. Soc. Rev.,  2014, 43(10), 3525-3550.
 [http://dx.doi.org/10.1039/C3CS60289C] [PMID:  24585151]

[47]
Chen, J.Q.; Li, J.H.; Dong, Z.B. A review on the latest progress of Chan-Lam coupling reaction. Adv. Synth. Catal.,  2020, 362(16), 3311-3331.
 [http://dx.doi.org/10.1002/adsc.202000495]

[48]
Munir, I.; Zahoor, A.F.; Rasool, N.; Naqvi, S.A.R.; Zia, K.M.; Ahmad, R. Synthetic applications and methodology development of Chan–Lam coupling: a review. Mol. Divers.,  2019, 23(1), 215-259.
 [http://dx.doi.org/10.1007/s11030-018-9870-z] [PMID:  30159807]

[49]
West, M.J.; Fyfe, J.W.B.; Vantourout, J.C.; Watson, A.J.B. Mechanistic development and recent applications of the Chan–Lam amination. Chem. Rev.,  2019, 119(24), 12491-12523.
 [http://dx.doi.org/10.1021/acs.chemrev.9b00491] [PMID:  31756093]

[50]
Hisana, K.N.; Afsina, C.M.A.; Anilkumar, G. Copper-catalyzed N -arylation of pyrroles: an overview. New J. Chem.,  2021, 45(37), 17061-17076.
 [http://dx.doi.org/10.1039/D1NJ02638K]

[51]
Marín, M.; Rama, R.J.; Nicasio, M.C. Ni-catalyzed amination reactions: an overview. Chem. Rec.,  2016, 16(4), 1819-1832.
 [http://dx.doi.org/10.1002/tcr.201500305] [PMID:  27265724]

[52]
Hayler, J.D.; Leahy, D.K.; Simmons, E.M. A pharmaceutical industry perspective on sustainable metal catalysis. Organometallics,  2019, 38(1), 36-46.
 [http://dx.doi.org/10.1021/acs.organomet.8b00566]

[53]
Gujjarappa, R.; Vodnala, N.; Malakar, C.C. Comprehensive strategies for the synthesis of isoquinolines: progress since 2008. Adv. Synth. Catal.,  2020, 362(22), 4896-4990.
 [http://dx.doi.org/10.1002/adsc.202000658]

[54]
Gujjarappa, R.; Vodnala, N.; Malakar, C.C. Recent advances in pyridine-based organocatalysis and its application towards valuable chemical transformations. ChemistrySelect,  2020, 5(28), 8745-8758.
 [http://dx.doi.org/10.1002/slct.202002765]

[55]
Reetu, R.; Gujjarappa, R.; Malakar, C.C. Recent advances in synthesis and medicinal evaluation of 1,2-benzothiazine analogues. Asian J. Org. Chem.,  2022, 11(8), e202200163.
 [http://dx.doi.org/10.1002/ajoc.202200163]

[56]
Malakar, C.C.; Dell’Amico, L.; Zhang, W. Dual catalysis in organic synthesis: current challenges and new trends. Eur. J. Org. Chem.,  2023, 26(1), e202201114.
 [http://dx.doi.org/10.1002/ejoc.202201114]

[57]
Aljaar, N.; Ibrahim, M.M.; Younes, E.A.; Al-Noaimi, M.; Abu-Safieh, K.A.; Ali, B.F.; Kant, K.; Al-Zaqri, N.; Sengupta, R.; Malakar, C.C. Strategies towards the synthesis of 2-ketoaryl azole derivatives using C-H functionalization approach and 1,2-bis-nucleophile precursors. Asian J. Org. Chem.,  2023, 12(4), e202300036.
 [http://dx.doi.org/10.1002/ajoc.202300036]

[58]
Patel, C.K.; Banerjee, S.; Kant, K.; Sengupta, R.; Aljaar, N.; Malakar, C.C. Roles of alkali metals tert-butoxide as catalysts and activators in organic transformations. Asian J. Org. Chem.,  2023, 12(8), e202300311.
 [http://dx.doi.org/10.1002/ajoc.202300311]

[59]
Kant, K.; Patel, C.K.; Banerjee, S.; Naik, P.; Atta, A.K.; Kabi, A.K.; Malakar, C.C. Recent advancements in strategies for the synthesis of imidazoles, thiazoles, oxazoles, and benzimidazoles. ChemistrySelect,  2023, 8(47), e202303988.
 [http://dx.doi.org/10.1002/slct.202303988]

[60]
Ananthu, S.; Aneeja, T.; Anilkumar, G. N-arylation of imidazoles: An overview. ChemistrySelect,  2021, 6(37), 9794-9805.
 [http://dx.doi.org/10.1002/slct.202102411]

[61]
Oeser, P.; Koudelka, J.; Petrenko, A.; Tobrman, T. Recent progress concerning the N-arylation of indoles. Molecules,  2021, 26(16), 5079.
 [http://dx.doi.org/10.3390/molecules26165079] [PMID:  34443667]

[62]
Crawford, S.M.; Lavery, C.B.; Stradiotto, M. BippyPhos: a single ligand with unprecedented scope in the Buchwald-Hartwig amination of (hetero)aryl chlorides. Chemistry,  2013, 19(49), 16760-16771.
 [http://dx.doi.org/10.1002/chem.201302453] [PMID:  24281816]

[63]
Chen, H.; Yang, H.; Li, N.; Xue, X.; He, Z.; Zeng, Q. Palladium-catalyzed C–N cross-coupling of NH-heteroarenes and quaternary ammonium salts via C–N bond cleavage. Org. Process Res. Dev.,  2019, 23(8), 1679-1685.
 [http://dx.doi.org/10.1021/acs.oprd.9b00194]

[64]
He, X.; Hu, S.; Xiao, Y.; Yu, L.; Duan, W. Access to ketones through palladium-catalyzed cross-coupling of phenol derivatives with nitroalkanes followed by nef reaction. Eur. J. Org. Chem.,  2022, 2022(35), e202200731.
 [http://dx.doi.org/10.1002/ejoc.202200731]

[65]
Yao, J.; Yu, L.; Duan, W.; Li, C.J. Palladium-catalyzed C–Si bond formation via denitrative cross-coupling of nitroarenes with hexamethyldisilane. Org. Chem. Front.,  2023, 10(2), 524-530.
 [http://dx.doi.org/10.1039/D2QO01764D]

[66]
Hu, S.; He, X.; Lei, Z.; Yu, L.; Duan, W. Palladium-catalyzed α-arylation of nitroalkanes with aryl triflates through the C(sp2)−C(sp3) bond coupling. J. Mol. Struct.,  2023, 1286, 135565.
 [http://dx.doi.org/10.1016/j.molstruc.2023.135565]

[67]
Liu, J.; Yao, J.; Du, J.; Yu, L.; Duan, W.; Xiao, Y.; Lei, Z. Direct synthesis of α-ketoamides via copper-catalyzed reductive amidation of nitroarenes with α-oxocarboxylic acids. J. Org. Chem.,  2024, 89(9), 6575-6583.
 [http://dx.doi.org/10.1021/acs.joc.4c00237] [PMID:  38656973]

[68]
Lei, Z.; Yao, J.; Xiao, Y.; Liu, W.H.; Yu, L.; Duan, W.; Li, C.J. Dual role of nitroarenes as electrophiles and arylamine surrogates in Buchwald–Hartwig-type coupling for C–N bond construction. Chem. Sci.,  2024, 15(10), 3552-3561.
 [http://dx.doi.org/10.1039/D3SC06618E] [PMID:  38455022]

[69]
Feng, L.; Yao, J.; Yu, L.; Duan, W. Palladium-catalyzed denitrative N -arylation of nitroarenes with pyrroles, indoles, and carbazoles. Org. Chem. Front.,  2022, 9(9), 2351-2356.
 [http://dx.doi.org/10.1039/D2QO00010E]

[70]
Paul, A.; Chatterjee, D.; Banerjee, S.; Yadav, S. Ligand and Cu free N -arylation of indoles, pyrroles and benzylamines with aryl halides catalyzed by a Pd nanocatalyst. New J. Chem.,  2020, 44(34), 14447-14452.
 [http://dx.doi.org/10.1039/D0NJ02129F]

[71]
Rull, S.G.; Funes-Ardoiz, I.; Maya, C.; Maseras, F.; Fructos, M.R.; Belderrain, T.R.; Nicasio, M.C. Elucidating the mechanism of aryl aminations mediated by NHC-supported nickel complexes: Evidence for a nonradical Ni(0)/Ni(ii) pathway. ACS Catal.,  2018, 8(5), 3733-3742.
 [http://dx.doi.org/10.1021/acscatal.8b00856]

[72]
McGuire, R.T.; Paffile, J.F.J.; Zhou, Y.; Stradiotto, M. Nickel-catalyzed C–N cross-coupling of ammonia, (hetero)anilines, and indoles with activated (hetero)aryl chlorides enabled by ligand design. ACS Catal.,  2019, 9(10), 9292-9297.
 [http://dx.doi.org/10.1021/acscatal.9b03715]

[73]
Morioka, T.; Nakatani, S.; Sakamoto, Y.; Kodama, T.; Ogoshi, S.; Chatani, N.; Tobisu, M. Nickel-catalyzed decarbonylation of N -acylated N-heteroarenes. Chem. Sci. (Camb.),  2019, 10(27), 6666-6671.
 [http://dx.doi.org/10.1039/C9SC02035G] [PMID:  31367320]

[74]
Malapit, C.A.; Borrell, M.; Milbauer, M.W.; Brigham, C.E.; Sanford, M.S. Nickel-catalyzed decarbonylative amination of carboxylic acid esters. J. Am. Chem. Soc.,  2020, 142(13), 5918-5923.
 [http://dx.doi.org/10.1021/jacs.9b13531] [PMID:  32207616]

[75]
Dindarloo Inaloo, I.; Majnooni, S.; Eslahi, H.; Esmaeilpour, M. N -Arylation of (hetero)arylamines using aryl sulfamates and carbamates via C–O bond activation enabled by a reusable and durable nickel(0) catalyst. New J. Chem.,  2020, 44(31), 13266-13278.
 [http://dx.doi.org/10.1039/D0NJ01610A]

[76]
Iranpoor, N.; Firouzabadi, H.; Etemadi Davan, E.; Rostami, A.; Nematollahi, A. Triphenyltin chloride as a new source of phenyl group for C-heteroatom and C–C bond formation. J. Organomet. Chem.,  2013, 740, 123-130.
 [http://dx.doi.org/10.1016/j.jorganchem.2013.04.053]

[77]
Toummini, D.; Tlili, A.; Bergès, J.; Ouazzani, F.; Taillefer, M. Copper-catalyzed arylation of nitrogen heterocycles from anilines under ligand-free conditions. Chemistry,  2014, 20(45), 14619-14623.
 [http://dx.doi.org/10.1002/chem.201404982] [PMID:  25284684]

[78]
Pawar, G.G.; Wu, H.; De, S.; Ma, D. Copper(i) oxide/N,N′-bis[(2-furyl)methyl]oxalamide-catalyzed coupling of (hetero)aryl halides and nitrogen heterocycles at low catalytic loading. Adv. Synth. Catal.,  2017, 359(10), 1631-1636.
 [http://dx.doi.org/10.1002/adsc.201700026]

[79]
Sharghi, H.; Sepehri, S.; Aberi, M. Cu(II) complex of pyridine-based polydentate as a novel, efficient, 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]

[80]
Minnick, J.L.; Domyati, D.; Ammons, R.; Tahsini, L. (X = N, O) cross-coupling reactions catalyzed by copper-pincer bis(N-heterocyclic carbene) complexes. Front Chem.,  2019, 7, 12.
 [http://dx.doi.org/10.3389/fchem.2019.00012] [PMID:  30766865]

[81]
Zhang, M.; Zhang, Y.; Zhang, H.; Zeng, Y.; Liu, G. N-heterocyclic carbene copper(I) complex catalyzed coupling of (hetero)aryl chlorides and nitrogen heterocycles: Highly efficient catalytic system. Chin. J. Chem.,  2020, 38(11), 1252-1256.
 [http://dx.doi.org/10.1002/cjoc.201900461]

[82]
Xie, Q.; Zhang, X.; Liu, H.; Zhang, F.; Luo, X.; Luo, H. Copper-catalyzed N-arylation of indoles and anilines with aryltrialkoxysilanes. Asian J. Org. Chem.,  2022, 11(3), e202100792.
 [http://dx.doi.org/10.1002/ajoc.202100792]

[83]
Wu, F.; Yan, F.; Wu, L.; Zhang, C.; Zeng, R.; Sun, Y.; Liu, X.; Cui, C.; Wang, P. Reduction system “vitamin C/glycerol” promoted copper(II)‐catalyzed N ‐arylation. Appl. Organomet. Chem.,  2022, 36(5), e6618.
 [http://dx.doi.org/10.1002/aoc.6618]

[84]
Németh, J.; Debreczeni, N.; Gresits, I.; Bálint, M.; Hell, Z. An efficient heterogeneous catalytic method for the N-arylation of pyrrole and other N-heterocycles. Catal. Lett.,  2015, 145(5), 1113-1119.
 [http://dx.doi.org/10.1007/s10562-015-1523-6]

[85]
Das, S.K.; Deka, P.; Chetia, M.; Deka, R.C.; Bharali, P.; Bora, U. Spherical CuO nanoparticles as catalyst for Chan–Lam cross-coupling reaction under base free condition. Catal. Lett.,  2018, 148(2), 547-554.
 [http://dx.doi.org/10.1007/s10562-017-2278-z]

[86]
Lü, X.; Ruan, J.; Chen, X.; Qian, C. Cross-linked chitosan bead supported copper complex in water as a green and efficient catalytic protocol for Ullmann reaction. Youji Huaxue,  2019, 39(6), 1720-1726.
 [http://dx.doi.org/10.6023/cjoc201901018]

[87]
Saikia, R.; Boruah, P.K.; Ahmed, S.M.; Das, M.R.; Thakur, A.J.; Bora, U. An avenue to Chan-Lam N-arylation by Cu(0) nanoparticles immobilized graphitic carbon-nitride oxide surface. Appl. Catal. A Gen.,  2022, 643, 118767.
 [http://dx.doi.org/10.1016/j.apcata.2022.118767]

[88]
Kaviani, N.; Behrouz, S.; Jafari, A.A.; Soltani Rad, M.N. Functionalization of Fe3O4@SiO2 nanoparticles with Cu(I)-thiosemicarbazone complex as a robust and efficient heterogeneous nanocatalyst for N-arylation of N-heterocycles with aryl halides. RSC Advances,  2023, 13(43), 30293-30305.
 [http://dx.doi.org/10.1039/D3RA06327E] [PMID:  37849694]

[89]
Mo, B.; Li, Z.; Peng, J.; Chen, C. Novel lignin-supported copper complex as a highly efficient and recyclable nanocatalyst for Ullmann reaction. Int. J. Biol. Macromol.,  2023, 239, 124263.
 [http://dx.doi.org/10.1016/j.ijbiomac.2023.124263] [PMID:  37004929]

[90]
Creutz, S.E.; Lotito, K.J.; Fu, G.C.; Peters, J.C. Photoinduced Ullmann C-N coupling: demonstrating the viability of a radical pathway. Science,  2012, 338(6107), 647-651.
 [http://dx.doi.org/10.1126/science.1226458] [PMID:  23118186]

[91]
Ziegler, D.T.; Choi, J.; Muñoz-Molina, J.M.; Bissember, A.C.; Peters, J.C.; Fu, G.C. A versatile approach 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]

[92]
Yoo, W.J.; Tsukamoto, T.; Kobayashi, S. Visible light-mediated Ullmann-type C–N coupling reactions of carbazole derivatives and aryl iodides. Org. Lett.,  2015, 17(14), 3640-3642.
 [http://dx.doi.org/10.1021/acs.orglett.5b01645] [PMID:  26151428]

[93]
Barange, S.H.; Bhagat, P.R. A metal/solvent/additive free compliant route to Ullmann-type C−N coupling using ionic liquid entangled porphyrin heterogeneous photocatalyst. ChemistrySelect,  2022, 7(35), e202201177.
 [http://dx.doi.org/10.1002/slct.202201177]

[94]
Mataghare, B.C.; Bhagat, P.R. Construction of porphyrin-based photocatalyst comprising pyridinium ionic liquid moiety for the metal-free visible light-assisted N-arylation of amines: facile approach to afford drug intermediates. New J. Chem.,  2023, 47(47), 21764-21780.
 [http://dx.doi.org/10.1039/D3NJ04295B]
Rights & Permissions Print Cite
Journal Information
For Authors
For Editors
For Reviewers
Explore Articles
Open Access
Open Access Articles
For Visitors
DOI https://dx.doi.org/10.2174/0113852728320325240710053300	Print ISSN 1385-2728
Publisher Name Bentham Science Publisher	Online ISSN 1875-5348
Current Organic Chemistry

Recent Advances in N-Arylation of Heterocycles in the Past Decade

Abstract Play Pause

Related Journals

Related Books

Abstract
