Advances on N-arylation of indoles by cross-coupling reactions

Mini-Reviews in Organic Chemistry

Volumn 6, Issue 4, 2009, Pages 367-377

  Xu, Hui ^a  

^a NORTHWEST A F UNIVERSITY   (China)

Author keywords

Aromatic nucleophilic substitution reaction; Cross coupling; Indole; N Arylindole; Transition metal catalyst

Indexed keywords

AROMATIC COMPOUNDS; CATALYSTS; NITROGEN COMPOUNDS; SUBSTITUTION REACTIONS; SULFUR COMPOUNDS; TRANSITION METALS;

AROMATIC NUCLEOPHILIC SUBSTITUTION REACTION; ARYL HALIDES; CROSS COUPLING REACTIONS; CROSS-COUPLINGS; ELECTRON-WITHDRAWING SUBSTITUENTS; INDOLE; N-ARYLATIONS; N-ARYLINDOLE; TRANSITION METAL CATALYSTS;

METAL HALIDES;

EID: 70350132020     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157019309789371613     Document Type: Article

References (39)

1. Von Angerer, E.; Strohmeier, J. 2-Phenylindoles. Effect of N-benzylation on estrogen receptor affinity, estrogenic properties, and mammary tumor inhibit-ing activity. J. Med. Chem., 1987, 30, 131-136.
2. Glamkowski, E. J.; Fortunato, J. M.; Spaulding, T. C.; Wilker, J. C.; Ellis, D. B. 3-(1-Indolinyl)benzylamines: A new class of analgesic agents. J. Med. Chem., 1985, 28, 66-73.
3. Unangst, P. C.; Carethers, M. E.; Webster, K.; Janik, G. M.; Robichaud, L. J. Acidic furo[3,2-b]indoles. A new series of potent antiallergy agents. J. Med. Chem., 1984, 27, 1629-1633.
4. Sano, H.; Noguchi, T.; Miyajima, A.; Hashimoto, Y.; Miyachi, H. Anti-angiogenic activity of basic-type, selective cyclooxygenase (COX)-1 inhibi-tors. Bioorg. Med. Chem. Lett., 2006, 16, 3068-3072.
5. Perregaard, J.; Arnt, J.; Boegesoe, K. P.; Hyttel, J.; Sanchez, C. Noncataleptogenic, centrally acting dopamine D-2 and serotonin 5-HT2 an-tagonists within a series of 3-substituted 1-(4-fluorophenyl)-1H-indoles. J. Med. Chem., 1992, 35, 1092-1101.
6. Cole, D. C.; Ellingboe, J. W.; Lennox, W. J.; Mazandarani, H.; Smith, D. L.; Stock, J. R.; Zhang, G. M.; Zhou, P.; Schechter, L. E. N1-Arylsulfonyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole derivatives are potent and selec-tive 5-HT6 receptor antagonists. Bioorg. Med. Chem. Lett., 2005, 15, 379-383.
7. Li, Q.; Li, T. M.; Woods, K. W.; Gu, W. Z.; Cohen, J.; Stoll, V. S.; Galicia, T.; Hutchins, C.; Frost, D.; Rosenberg, S. H.; Sham, H. L. Benzimidazolones and indoles as non-thiol farnesyltransferase inhibitors based on tipifarnib scaffold: synthesis and activity. Bioorg. Med. Chem. Lett., 2005, 15, 2918-2922.
8. 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., 2008, 56, 720-722.
9. Pozharskii, A. F.; Martsokha, B. K.; Simonov, A. M. Direct N-arylation of five-membered heterocycles. Zh. Obshch. Khim., 1963, 33, 1005-1007.
10. Barton, D. H. R.; Blazejewski, J. C.; Charpiot, B.; Finet, J. P.; Mother-well, W. B.; Papoula, M. T. B.; Stanforth, S. P. Phenylation of enols and of enolate and other anions. J. Chem. Soc., Perkin Trans. I, 1985, 2667-2675;
11. Bartona, D. H. R.; Fineta, J. P.; Khamsia, J. Copper catalysed phenylation of indoles by triphenylbismuthBIS-trifluoroacetate. Tetrahedron Lett., 1988, 29, 1115-1118;
12. Brown, R. A.; Fernando, S. I. S.; Roberts, R. M. G. De-complexation of (-arene)(-cyciopentadienyl)iron(II) hexafluorophos-phates: A convenient one-pot arylation procedure. J. Chem. Soc., Perkin Trans. 1, 1994, 197-201.
13. Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. Catalytic cross-coupling reactions mediated by palladium/nucleophilic car-bene systems. J. Organomet. Chem., 2002, 653, 69-82.
14. Stabler, S. R.; Jahangir. Preparation of N-arylated heterocycles by nu-cleophilic aromatic substitution. Synth. Commun., 1994, 24, 123-129
15. Seki, K.; Ohkura, K.; Terashima, M.; Kanaoka, Y. A facile synthesis of N-(2-pyridyl and 4-pyridyl)indoles. Heterocycles, 1994, 37, 993-996
16. Smith III W. J.; Sawyer, J. S. A novel and selective method for the N-arylation of indoles mediated by KF/Al2O3. Tetrahedron Lett., 1996, 37, 299-302
17. 2) bond formation: N-Arylation of aromatic and unsatu-rated nitrogen and the reductive elimination chemistry of palladium azolyl and methyleneamido complexes. J. Am. Chem. Soc., 1998, 120, 827-828.
18. Old, D. W.; Harris, M. C.; Buchwald, S. L. Efficient palladium-catalyzed N-arylation of indoles. Org. Lett., 2000, 2, 1403-1406.
19. Grasa, G. A.; Viciu, M. S.; Huang, J. K.; Nolan, S. P. Amination reactions of aryl halides with nitrogen-containing reagents mediated by palla-dium/imidazolium salt systems. J. Org. Chem., 2001, 66, 7729-7737
20. Huang, X. H.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. Expanding Pd-catalyzed C-N bond-forming processes: The first amida-tion of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions. J. Am. Chem. Soc., 2003, 125, 6653-6655.
21. Klapars, A.; Antilla, J. C.; Huang, X. H.; 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, 7727-7729
22. Antilla, J. C.; Klapars, A.; Buchwald, S. L. The copper-catalyzed N-arylation of indoles. J. Am. Chem. Soc., 2002, 124, 11684-11688.
23. Zhang, H.; Cai, Q.; Ma, D. W. Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocy-cles. J. Org. Chem., 2005, 70, 5164-5173.
24. Kuil, M.; Bekedam, E. K.; Visser, G. M.; van den Hoogenband, A.; Terpstra, J. W.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; van Strijdonck, G. P. F. Mild copper-catalyzed N-arylation of azaheterocycles with aryl halides. Tetrahedron Lett., 2005, 46, 2405-2409.
25. Deng, W.; Wang, Y. F.; Zhang, C.; Liu, L.; Guo, Q. X. CuI/proline-catalyzed N-arylation of nitrogen heterocycles. Chin. Chem. Lett., 2006, 17, 313-316
26. Bellina, F.; Calandri, C.; Cauteruccio, S.; Rossi, R. Selective, efficient and functional group-tolerant CuOAc-mediated N-arylation of 1H-indoles and 9H-carbazole with aryl iodides under base-free and ligandless conditions. Eur. J. Org. Chem., 2007, 2147-2151.
27. Bekolo, H. Copper-mediated N-arylation of electron-deficient pyrroles and indoles. Can. J. Chem., 2007, 85, 42-46.
28. Chang, J. W. W.; Xu, X. H.; Chan, P. W. H. Practical copper-catalyzed N-arylartion of nitrogen heterocycles with aryl halides under ligand and addi-tive free conditions. Tetrahedron Lett., 2007, 48, 245-248.
29. Tang, B. X.; Guo, S. M.; Zhang, M. B.; Li, J. H. N-Arylartion of nitrogen-containing heterocycles with aryl and heteroaryl halides using a copper(I) ox-ide nanoparticle/1,10-phenanthroline catalytic system. Synthesis, 2008, 1707-1716.
30. Periasamy, M.; Vairaprakash, P.; Dalai, M. New diimine-copper complexes: An efficient and simple catalyst system for Buchwald N-arylation of indole. Organometallics, 2008, 27, 1963-1966.
31. Xue, F.; Cai, C. Y.; Sun, H. M.; Shen, Q.; Rui, J. -Ketoimine as an efficient ligand for copper-catalyzed N-arylation of nitrogen-containing heterocycles with aryl halides. Tetrahedron Lett., 2008, 49, 4386-4389.
32. Xi, Z. X.; Liu, F. H.; Zhou, Y. B.; Chen, W. Z. CuI/L (L=pyridine-functionalized 1,3-diketones) catalyzed C-N coupling reactions of aryl hal-ides with NH-containing heterocycles. Tetrahedron, 2008, 64, 4254-4259
33. Correa, A.; Bolm, C. Iron-catalyzed N-arylation of nitrogen nucleophiles. Angew. Chem. Int. Ed., 2007, 46, 8862-8863.
34. Rout, L.; Saha, P.; Jammi, S.; Punniyamurthy, T. Cadmium(II)-catalyzed C -N cross-coupling of amines with aryl iodides. Adv. Synth. Catal., 2008, 350, 395-398.
35. Maiorana, S.; Baldoli, C.; Buttero, P. D.; Ciolo, M. D.; Papagni, A. Aromatic nucleophilic substitution on haloarene chromium tricarbonyl complexes: Mild N-arylation of indoles. Synthesis, 1998, 735-738.
36. Smith III W. J.; Sawyer, J. S. An SNAr-base preparation of 1-(2-,3-, and 4-p yridyl)indoles using KF/Al2O3. Heterocycles, 1999, 51, 157-160
37. 2) bond formation by aromatic nucleophilic substitution reactions. Z. Naturforsch., 2008, 63B, 298-302.
38. Xu, H.; Lv, L.; Fan, L. L.; He, X. Q. Ultrasound-assisted N-arylation of indoles without any catalyst. Heterocycles, 2008, 76, 249-256
39. Frayne, G. L.; Green, G. M. Investigation of the N-arylation of various substituted indoles using microwave-assisted technology. Tetrahedron Lett., 2008, 49, 7328-7329.