Palladium-catalyzed synthesis of selectively substituted phenanthridine derivatives

Advanced Synthesis and Catalysis

Volumn 350, Issue 16, 2008, Pages 2513-2516

  Della Ca', Nicola ^a   Motti, Elena ^a   Catellani, Marta ^a  

^a UNIVERSITY OF PARMA   (Italy)

Author keywords

C H activation; Catalysis; Norbornene; Palladium; Phenanthridines; Sequential reactions

Indexed keywords

EID: 56649086815     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800512     Document Type: Article

References (35)

1. a) A. R. Katritzky, C. W. Rees, E. F. Scriven, (Eds.), Comprehensive Heterocyclic Chemistry II, Pergamon, Oxford, 1996;
2. b) A. J. Molinari, M. A. Ashwell, B. H. Ridgway, A. A. Failli, W. J. Moore, (Wyeth), US Patent 6,894,061 B2, 2005;
3. c) B. H. Ridgway, W. J. Moore, M. A. Ashwell, W. R. Solvibile, A. T.-T. Lee, M. E. Hoke, M. Antane, A. A. Failli, (Wyeth), PCT Int. Appl. WO 2006009831 A1, 2006; Chem. Abstr. 2006, 144, 170896.
4. a) L. F. Tietze, G. Brasche, K. M. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006;
5. b) J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester, 2004;
6. c) E.-I. Negishi, A. de Meijere, (Eds.), Handbook of Organopalladium Chemistry for Organic Synthesis, Wiley-Interscience, New York, 2002.
7. a) F. Faccini, E. Motti, M. Catellani, J. Am. Chem. Soc. 2004, 126, 78-79;
8. b) R. Ferraccioli, D. Carenzi, O. Rombolà, M. Catellani, Org. Lett. 2004, 6, 4759-4762;
9. c) M. Catellani, E. Motti, N. Della Ca', Acc. Chem. Res. 2008, ASAP;
10. d) B. Mariampillai, J. Alliot, M. Li, M. Lautens, J. Am. Chem. Soc. 2007, 129, 15372-15379.
11. a) E. Motti, F. Faccini, I. Ferrari, M. Catellani, R. Ferraccioli, Org. Lett. 2006, 8, 3967-3970;
12. b) E. Motti, N. Della Ca', R. Ferraccioli, M. Catellani, Synthesis 2007, 995-997.
13. N. Della Ca', G. Sassi, M. Catellani, Adv. Synth. Catal. 2008, 350, 2179-2182.
14. A similar positive effect was observed by Miura and co-workers who reported the synthesis of phenanthridine derivatives by oxidative cross-coupling of N-(2′-phenylphenyl)benzenesulfonamides with olefins using a palladium-copper catalytic system: M. Miura, T. Tsuda, T. Satoh, S. Pivas-Art, M. Nomura, J. Org. Chem. 1998, 63, 5211-5215.
15. a) P. Fitton, E. A. Rick, J. Organomet. Chem. 1971, 28, 287-291;
16. b) A. H. Roy, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 13944-13945.
17. a) H. Horino, M. Arai, N. Inoue, Tetrahedron Lett. 1974, 647-650;
18. b) C.-S. Li, C.-H. Cheng, F.-L. Liao, S.-L. Wang, Chem. Commun. 1991, 710-712;
19. c) M. Portnoy, Y. Ben-David, I. Rousso, D. Milstein, Organometallics 1994, 13, 3465-3479;
20. d) M. Catellani, C. Mealli, E. Motti, P. Paoli, E. Perez-Carreno, P. S. Pregosin, J. Am. Chem. Soc. 2002, 124, 4336-4346.
21. a) G. Dyker, Angew. Chem. Int. Ed. 1999, 38, 1699-1712;
22. b) F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003, 345, 1077-1101;
23. c) L.-C. Campeau, K. Fagnou, Chem. Commun. 2006, 1253-1264;
24. d) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174-238.
25. a) I. P. Beletskaya, A. V. Cheprakov, J. Organometal. Chem. 2004, 689, 4055-4082;
26. b) M. Catellani, G. P. Chiusoli, J. Organomet. Chem. 1992, 425, 151-154;
27. c) M. Catellani, G. P. Chiusoli, J. Organomet. Chem. 1988, 346, C27-C30;
28. d) C.-H. Liu, C.-S. Li, C.-H. Cheng, Organometallics 1994, 13, 18-20.
29. a) A. J. Canty, Acc. Chem. Res. 1992, 25, 83-90;
30. b) M. Catellani, M. C. Fagnola, Angew. Chem. Int. Ed. 1994, 33, 2421-2422;
31. c) S. R. Whitfield, M. S. Sanford, J. Am. Chem. Soc. 2007, 129, 15142-15143.
32. This result also rules out the possibility that the reaction leading to 4 proceeds through an alternative pathway consisting of methyl o-methylcinnamate formation, Michael addition of the arenesulfonyl o-bromoaniline and final intramolecular arylation in sequence. This alternative pathway to 4 was further excluded on the ground that methyl o-methylcinnamate and o-bromo-N-tosylaniline did not react under the reaction conditions.
33. 4I.
34. C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321.
35. T. Jeffery, Tetrahedron 1996, 52, 10113-10130.