Palladium-catalyzed domino direct arylation/n-arylation: convenient synthesis of phenanthridines

Angewandte Chemie - International Edition

Volumn 48, Issue 36, 2009, Pages 6713-6716

  Candito, David A ^a   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

C h activation; Domino reactions; Imines n arylation; Palladium

Indexed keywords

ARYLATIONS; C-H ACTIVATION; DOMINO REACTIONS; IMINES N-ARYLATION; PHENANTHRIDINE; STARTING MATERIALS; TERT-BUTYLDIMETHYLSILYL; TRIMETHYLSILYL;

ACTIVATION ANALYSIS; NITROGEN COMPOUNDS; PALLADIUM; REACTION KINETICS;

AROMATIC COMPOUNDS;

ORGANOMETALLIC COMPOUND; PALLADIUM; PHENANTHRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CATALYSIS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHENANTHRIDINES;

EID: 70349921519     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200902400     Document Type: Article

References (46)

1. a) D. Makhey, B. Gatto, C. Yu, A. Liu, L. F. Liu, E. J. LaVoie, Bioorg. Med. Chem. 1996, 4, 781-791;
2. b) M. A. Lynch, O. Duval, A. Sukhanova, J. Devy, S. P. MacKay, R. D. Waigh, I. Nabiev, Bioorg. Med. Chem. Lett. 2001, 11, 2643-2646;
3. c) S. D. Fang, L. K. Wang, S. M. Hecht, J. Org. Chem. 1993, 58, 5025-5027;
4. d) Y. L. Janin, A. Croisy, J. F. Riou, E. Bisagni, J. Med. Chem. 1993, 36, 3686-3692.
5. Synthetic approaches to phenanthridines: a) S. P. Marsden, A. E. McGonagle, B. McKeever-Abbas, Org. Lett. 2008, 10, 2589-2591;
6. b) R. Alonso, P. J. Campos, B. Garcia, M. A. Rodriguez, Org. Lett. 2006, 8, 3521-3523;
7. c) B. K. Mehta, K. Yanagisawa, M. Shiro, H. Kotsuki, Org. Lett. 2003, 5, 1605-1608;
8. d) J. Pawlas, M. Begtrup, Org. Lett. 2002, 4, 2687-2690;
9. e) M. Lysen, J. L. Kristensen, P. Vedso, M. Begtrup, Org. Lett. 2002, 4, 257-259;
10. f) R. Yanada, K. Hashimoto, R. Tokizane, Y Miwa, H. Minami, K. Yanada, M. Ishikura, Y Takemoto, J. Org. Chem. 2008, 73, 5135-5138;
11. g) W.G. Shou, Y.-Y. Yang, Y.-G. Wang, J. Org. Chem. 2006, 71, 92419243;
12. h) B. Clement, M. Weide, U. Wolschendorf, I. Kock, Angew. Chem. 2005, 117, 641-645;
13. Angew. Chem. Int. Ed. 2005, 44, 635638.
14. Palladium-catalyzed approaches for the synthesis of phenanthridines: a) T. Gerfaud, L. Neuville, J. Zhu, Angew. Chem. 2009, 121, 580-585;
15. Angew. Chem. Int. Ed. 2009, 48, 572-577;
16. b) W. R. Bowman, J. E. Lyon, G. J. Pritchard, Synlett 2008, 2169-2171;
17. c) L. Sripada, J. A. Teske, A. Deiters, Org. Biomol. Chem. 2008, 6, 263-265;
18. d) N. Della Cá, E. Motti, M. Catellani, Adv. Synth. Catal. 2008, 350, 2513-2516;
19. e) M. G. Banwell, D. W. Lupton, X. Ma, J. Renner, M. O. Sydnes, Org. Lett. 2004, 6, 2741-2744;
20. f) D. Shabashov, O. Daugulis, J. Org. Chem. 2007, 72, 1110-1115;
21. g) C. Xie, Y. Zhang, Z. Huang, P. Xu, J. Org. Chem. 2007, 72, 5431 5434.
22. For reviews on this subject, see: a) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174-238;
23. b) L.-C. Campeau, K. Fagnou, Chem. Commun. 2006, 1253-1264;
24. c) M. Miura, T. Satoh, Top. Organomet. Chem. 2005, 14, 55-83;
25. d) Handbook of C.-H. Transformations (Ed.: G. Dyker), Wiley-VCH, Weinheim, 2005.
26. a) M. Catellani, M. C. Fagnola, Angew. Chem. 1994, 106, 25592561;
27. Angew. Chem. Int. Ed. Engl. 1994, 33, 2421-2422;
28. b) M. Catellani, Synlett 2003, 298-313;
29. c) E. Motti, G. Ippomei, S. Deledda, M. Catellani, Synthesis 2003, 2671-2678;
30. d) F., Faccini, E. Motti, M. Catellani, J. Am. Chem. Soc. 2004, 126, 78-79.
31. a) P. Thansandote, C. Gouliaras, M.-O. Turcotte-Savard, M. Lautens, J. Org. Chem. 2009, 74, 1791-1793;
32. b) P. Thansandote, M. Raemy, A. Rudolph, M. Lautens, Org. Lett. 2007, 9, 5255-5258.
33. a) Y.-B. Zhao, B. Mariampillai, D. A. Candito, B. Laleu, M. Li, M. Lautens, Angew. Chem. 2009, 121, 1881-1884;
34. Angew. Chem. Int. Ed. 2009, 48, 1849-1852;
35. 3 (3.0 equiv), norbornene (3.0 equiv) in MeCN (0.05 M) were heated in a sealed tube which was placed in an oil bath (9O°C) for 16-24 h.
36. a) J. Barluenga, F. Aznar, C. Valdés, Angew. Chem. 2004, 116, 347-349;
37. Angew. Chem. Int. Ed. 2004, 43, 343-345;
38. b)J. P. Wolfe, J. Åhman, J. P. Sadighi, R. A. Singer, S. L. Buchwald, Tetrahedron Lett. 1997, 38, 6367-6370;
39. c) G. Mann, J. F. Hartwig, M. S. Driver, C. Fernandez-Rivas, J. Am. Chem. Soc. 1998, 120, 827-828;
40. d) C. Bolm, J. P. Hildebrand, J. Org. Chem. 2000, 65, 169-175;
41. e) K. R. Roesch, R. C. Larock, J. Org. Chem. 1998, 63, 5306-5307;
42. f) K. R. Roesch, H. Zhang, R. C. Larock, J. Org. Chem. 2001, 66, 8042-8051.
43. a) D. J. Hart, K. Kanai, D. G. Thomas, T.-K. Yang, J. Org. Chem. 1983, 48, 289-294, and references therein;
44. b) L.-H. Chan, E. G. Rochow, J. Organomet. Chem. 1967, 9, 231-250;
45. c) S. Lou, P. N. Moquist, S. E. Schaus, J. Am. Chem. Soc. 2007, 129, 15398 -15404 ;
46. d) H. Ahlbrecht, E.-O. Düber, Synthesis 1982, 273-275.