Citation:
Wei Liu, Li-Ya Han, Rui-Li Liu, Li-Ge Xu, Yan-Lan Bi. Copper-catalyzed N-arylation of 2-arylindoles with aryl halides[J]. Chinese Chemical Letters,
;2014, 25(9): 1240-1243.
doi:
10.1016/j.cclet.2014.04.021
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10 mol% CuI combined with the DMEDA ligand can efficiently catalyze the N-arylation of 2-arylindoles with aryl iodides and aryl bromides in good to excellent yields. The aryl halides bearing electron-rich or electron-deficient functional groups can be well tolerated under this mild reaction conditions.
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Keywords:
- 2-Arylindoles,
- Aryl halides,
- N-Arylation,
- Copper
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[1]
[1] S.V. Ley, A.W. Thomas, Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation, Angew. Chem. Int. Ed. Engl. 42 (2003) 5400-5449.
-
[2]
[2] F. Monnier, M. Taillefer, Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions: copper makes a difference, Angew. Chem. Int. Ed. Engl. 47 (2008) 3096-3099.
-
[3]
[3] Y. Wang, J. Zeng, X. Cui, Recent progress in copper-catalyzed C-N coupling reactions, Chin. J. Org. Chem. 30 (2010) 181-199.
-
[4]
[4] J.D. Senra, L.C.S. Aguiar, A.B.C. Simas, Recent progress in transition-metal catalyzed C-N cross-couplings: emerging approaches towards sustainability, Curr. Org. Synth. 8 (2011) 53-78.
-
[5]
[5] A. Klapars, J.C. Antilla, X. Huang, S.L. Buchwald, A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles, J. Am. Chem. Soc. 123 (2001) 7727-7729.
-
[6]
[6] J.C. Antilla, A. Klapars, S.L. Buchwald, The copper-catalyzed N-arylation of indoles, J. Am. Chem. Soc. 124 (2002) 11684-11688.
-
[7]
[7] A. Klapars, X. Huang, S.L. Buchwald, A general and efficient copper catalyst for the amidation of aryl halides, J. Am. Chem. Soc. 124 (2002) 7421-7428.
-
[8]
[8] H. Cristau, P.P. Cellier, J. Spindler, M. Taillefer, Highly efficient and mild coppercatalyzed N-and C-arylations with aryl bromides and iodides, Chem. Eur. J. 10 (2004) 5607-5622.
-
[9]
[9] X. Diao, Y. Wang, Y. Jiang, D. Ma, Assembly of substituted 1H-benzimidazoles and 1,3-dihydrobenzimidazol-2-ones via CuI/L-proline catalyzed coupling of aqueous ammonia with 2-iodoacetanilides and 2-iodophenylcarbamates, J. Org. Chem. 74 (2009) 7974-7977.
-
[10]
[10] R.K. Rao, A.B. Naidu, E.A. Jaseer, G. Sekar, An efficient, mild, and selective Ullmanntype N-arylation of indoles catalyzed by copper(I) complex, Tetrahedron 65 (2009) 4619-4624.
-
[11]
[11] A.K. Verma, J. Singh, R.C. Larock, Benzotriazole: an efficient ligand for the copper-catalyzed N-arylation of indoles, Tetrahedron 65 (2009) 8434-8439.
-
[12]
[12] S. Haneda, Y. Adachi, M. Hayashi, Copper(I)-2-(20-pyridyl)benzimidazole catalyzed N-arylation of indoles, Tetrahedron 65 (2009) 10459-10462.
-
[13]
[13] X. Yang, H. Xing, Y. Zhang, et al., CuI/8-hydroxyquinalidine promoted N-arylation of indole and azoles, Chin. J. Chem. 30 (2012) 875-880.
-
[14]
[14] F. Wu, P. Liu, X. Ma, J. Xie, B. Dai, Tetrazole-1-acetic acid as a ligand for coppercatalyzed N-arylation of imidazoles with aryl iodides under mild conditions, Chin. Chem. Lett. 24 (2013) 893-896.
-
[15]
[15] J. Engel-Andreasen, B. Shimpukade, T. Ulven, Selective copper catalysed aromatic N-arylation in water, Green Chem. 15 (2013) 336-340.
-
[16]
[16] L.B. Zhu, L. Cheng, Y.X. Zhang, R.G. Xie, J.S. You, Highly efficient copper-catalyzed N-arylation of nitrogen-containing heterocycles with aryl and heteroaryl halides, J. Org. Chem. 72 (2007) 2737-2743.
-
[17]
[17] L.B. Zhu, G.C. Li, L. Luo, et al., Highly functional group tolerance in coppercatalyzed N-arylation of nitrogen-containing heterocycles under mild conditions, J. Org. Chem. 74 (2009) 2200-2202.
-
[18]
[18] N. Panda, A.K. Jena, S. Mohapatra, S.R. Rout, Copper ferrite nanoparticle-mediated N-arylation of heterocycles: a ligand-free reaction, Tetrahedron Lett. 52 (2011) 1924-1927.
-
[19]
[19] N.V. Suramwar, S.R. Thakare, N.N. Karade, N.T. Khaty, Green synthesis of predominant (1 1 1) facet CuO nanoparticles: heterogeneous and recyclable catalyst for N-arylation of indoles, J. Mol. Cat. A: Chem. 359 (2012) 28-34.
-
[20]
[20] F.P. Yi, H.Y. Sun, X.H. Pan, Y. Xu, J.Z. Li, Synthesis of Fischer indole derivatives using carboxyl-functionalized ionic liquid as an efficient and recyclable catalyst, Chin. Chem. Lett. 20 (2009) 275-278.
-
[21]
[21] S.V. Goswami, P.B. Thorat, V.N. Kadam, S.A. Khiste, S.R. Bhusare, A convenient one-pot three component synthesis of 3-aminoalkylated indoles catalyzed by 3-chlorophenylboronic acid, Chin. Chem. Lett. 24 (2013) 422-424.
-
[22]
[22] W.J. Smith III, J.S. Sawyer, A novel and selective method for the N-arylation of indoles mediated by KF/Al2O3, Tetrahedron Lett. 37 (1996) 299-302.
-
[23]
[23] G.L. Frayne, G.M. Green, Investigation of the N-arylation of various substituted indoles using microwave-assisted technology, Tetrahedron Lett. 49 (2008) 7328-7329.
-
[24]
[24] Z.W. Chen, N. Zhang, Z.H. Wang, W.K. Su, An efficient synthesis of novel chromeno[3'4':5,6]pyrano[2,3-b]indole derivatives, Chin. Chem. Lett. 24 (2013) 199-201.
-
[25]
[25] Y.X. Cui, L.D. Sun, Q. Sun, L. Shi, Highly selective synthesis of 3-methylindole from glycerol and aniline over Cu/NaY modified by K22O, Chin. Chem. Lett. 24 (2013) 1127-1129.
-
[26]
[26] L. Ackermann, General and efficient indole syntheses based on catalytic amination reactions, Org. Lett. 7 (2005) 439-442.
-
[27]
[27] L.T. Kaspar, L. Ackermann, Three-component indole synthesis using ortho-dihaloarenes, Tetrahedron 61 (2005) 11311-11316.
-
[28]
[28] N.P. Bizier, J.W. Wackerly, E.D. Braunstein, et al., An alternative role for acetylenes: activation of fluorobenzenes toward nucleophilic aromatic substitution, J. Org. Chem. 78 (2013) 5987-5998.
-
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