Aromatic nucleophilic substitution on haloarene chromium tricarbonyl complexes: Mild N-arylation on indoles

Synthesis

Volumn , Issue 5, 1998, Pages 735-738

  Maiorana, Stefano ^a   Baldoli, Clara ^a   Del Buttero, Paola ^a   Di Ciolo, Michela ^a   Papagni, Antonio ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Aromatic nucleophilic substitution; Arylation; Haloarene chromium tricarbonyl complexes; Indole

Indexed keywords

CHROMIUM DERIVATIVE; HALOARENE CHROMIUM TRICARBONYL COMPLEX; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 0031966783     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2058     Document Type: Article

References (32)

1. Chapleo, R. B.; Fagan, G. P. Ann. Drug Data Report 1993, 15, 59.
2. Perregaard, J.; Arnt, J.; Bogeso, K. P.; Hyttel, J.; Sanchez, C. J. Med. Chem. 1992, 35, 1092.
3. Von Angerer, E.; Strohmeier, J. J. Med. Chem. 1987, 30, 131.
4. Glamkowsky, E. J.; Fortunato, J. M.; Spaulding, T. C.; Wilker, J. C.; Ellis, D. B. J. Med. Chem. 1985, 28, 66.
5. Unangst, P. C.; Carethers, M. E.; Webster, K.; Janik, G. M.; Robichaud, L. J. J. Med. Chem. 1984, 27, 1629.
6. (a) Barton, D. H. R.; Blazejewsky, J. C.; Charpiot, B.; Finet, J. P.; Motherwell, W. B.; Papoula, M. T. B.; Stanforth, S. P. J. Chem. Soc., Perkin Trans. I 1985, 2667.
7. (b) Barton, D. H. R.; Finet, J. P.; Khansi, J. Tetrahedron Lett. 1988, 29, 1115.
8. (c) Brown, R. A.; Fernando, S. I.; Roberts, R. M. J. Chem. Soc., Perkin Trans. I 1994, 197.
9. (d) Tokmakmov, G. P.; Grandberg, J. Tetrahedron 1995, 51, 2091.
10. Pozharskii, A. F.; Marsokha, B. K.; Simonov, A. M. J. Gen. Chem. USSR 1963, 33, 994.
11. Stabler, R. S.; Jahangir, Synth. Commun. 1994, 24, 123.
12. Seki, K.; Ohkura, K.; Terashima, M.; Kanaoka, Y. Heterocycles 1994, 37, 993.
13. Smith III, W. J.; Sawyer, S. Tetrahedron Lett. 1996, 37, 299.
14. Semmelhack, M. F. In Comprehensive Organometallic Chemistry II; Vol 12, Abel, E. W.; Stone, F. G. A.; Wilkenson, G., Eds.; Pergamon: New York, 1995; p 979.
15. Semmelhack, M. F. In Comprehensive Organic Synthesis; Trost, B. M., Ed; Pergamon: Oxford, 1991; p 517.
16. Astruc, D.; Balas, L.; Jhurry, D.; Latxague, L.; Grelier, S.; Morel, Y.; Hamdani, M.; Ardoin, N. Bull. Soc. Chim. Fr. 1990, 401.
17. Bunnet, J. F.; Hermann, H. J. Org. Chem. 1971, 36, 4081.
18. Houghton, R. P.; Voyle, M.; Price, R. J. Organomet. Chem. 1983, 259, 183.
19. Ghavshov, M.; Widdoson, D.A. J. Chem. Soc., Perkin Trans. I 1983, 3065.
20. Keller, L.; Time-Marshall, K.; Behar, S.; Richards, K. Tetrahedron Lett. 1989, 30, 3373.
21. Baldoli, C.; Del Buttero, P.; Maiorana, S. Tetrahedron Lett. 1992, 33, 4049.
22. Perez, M.; Potier, P.; Halazy, S. Tetrahedron Lett. 1996, 37, 8487.
23. Hong, F. E.; Lo, S. H.; Liou, M. W.; Chou, L. F.; Lin, C. C. J. Organomet. Chem. 1996, 516, 123.
24. 8 but no arylation product was obtained. No products of cine or tele substitution were detected. For ref. see:
25. Rose-Munch, F.; Rose, E.; Semra, A.; Bois, C. J. Organomet. Chem. 1989, 363, 103.
26. Rose-Munch, F.; Rose, E.; Semra, A.; Mignon, L.; Garcia-Orican, J. J. Organomet. Chem. 1989, 363, 297.
27. Reactions on fluoroarene complexes 2a-f worked in comparable yields even using DME as solvent.
28. Toritsuka, K. Jpn Patent 04, 319, 959, 1992; Chem. Abstr. 1993, 118, 202029g.
29. Gerard-Monier, D.; Erdelmeier, I.; Chaudiere, J. R.; Yadan, J. C. Fr. Patent 2, 704, 947, 1993; Chem. Abstr. 1995, 122, 128088q.
30. Alemagna, A.; Cremonesi, P.; Del Buttero, P.; Licandro, E.; Maiorana, S. J. Org. Chem. 1983, 48, 3114.
31. Dictionary of Organic Compounds, 5th ed., Vol.V; Buckingham J., Ed.; Chapman and Hall: New York, 1982.
32. Begtrup, M.; Elguero, J.; Faure, R.; Camps, P.; Estopa, C.; Ilavsky, D.; Fruchier, A.; Marzin, C.; de Mendoza, J. Magn. Res. Chem. 1988, 26, 134.