Intramolecular Pd(II)-catalyzed aerobic oxidative amination of alkenes: Synthesis of six-membered N-heterocycles

Organic Letters

Volumn 14, Issue 5, 2012, Pages 1234-1237

  Lu, Zhan ^a   Stahl, Shannon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; MACROCYCLIC COMPOUND; PALLADIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALKENES; AMINATION; CATALYSIS; CYCLIZATION; MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM;

EID: 84857826935     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300030w     Document Type: Article

References (55)

1. Wijtmans, R.; Vink, M. K. S.; Schoemaker, H. E.; van Delft, F. L.; Blaauw, R. H.; Rutjes, F. P. J. T. Synthesis-Stuttgart 2004, 641-662
2. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127-2198
3. Álvarez-Corral, M.; Muñoz-Dorado, M.; Rodríguez- García, I. Chem. Rev. 2008, 108, 3174-3198
4. Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395-3442
5. Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795-3892
6. Candeias, N. R.; Branco, L. C.; Gois, P. M. P.; Afonso, C. A. M.; Trindade, A. F. Chem. Rev. 2009, 109, 2703-2802
7. Majumdar, K. C.; Chattopadhyay, B.; Maji, P. K.; Chattopadhyay, S. K.; Samanta, S. Heterocycles 2010, 81, 795-866
8. Hegedus, L. S. In Comprehensive Organic Synthesis; Semmelhack, M. F., Ed.; Pergamon Press, Inc.: Elmsford, NY, 1991; Vol. 4, pp 551-569.
9. Hosokawa, T.; Murahashi, S.-I. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.; de Meijere, A., Eds.; John Wiley and Sons, Inc.: New York, 2002; Vol. 2, pp 2169-2192.
10. Hosokawa, T. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.; de Meijere, A., Eds.; John Wiley and Sons, Inc.: New York, 2002; Vol. 2, pp 2211-2225.
11. Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285-2309
12. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644-4680
13. Minatti, A.; Muñiz, K. Chem. Soc. Rev. 2007, 36, 1142-1152
14. Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318-5365
15. Kotov, V.; Scarborough, C. C.; Stahl, S. S. Inorg. Chem. 2007, 46, 1910-1923
16. Wolfe, J. P. Synlett 2008, 2913-2937
17. McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981-3019
18. Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420
19. Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221-229
20. Tamaru, Y.; Hojo, M.; Kawamura, S.-i.; Yoshida, Z.-i. J. Org. Chem. 1986, 51, 4089-4090
21. Takemiya, A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 6042-6043
22. Han, X.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2006, 45, 1747-1749
23. Nakhla, J. S.; Wolfe, J. P. Org. Lett. 2007, 9, 3279-3282
24. Stubbert, B. D.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 4253-4271
25. Leathen, M. L.; Rosen, B. R.; Wolfe, J. P. J. Org. Chem. 2009, 74, 5107-5110
26. Wu, L.; Qiu, S.; Liu, G. Org. Lett. 2009, 11, 2707-2710
27. Rice, G. T.; White, M. C. J. Am. Chem. Soc. 2009, 131, 11707-11711
28. Wu, T.; Yin, G.; Liu, G. J. Am. Chem. Soc. 2009, 131, 16354-16355
29. Balázs, Á.; Hetényi, A.; Szakonyi, Z.; Sillanpää, R.; Fülöp, F. Chem.-Eur. J. 2009, 15, 7376-7381
30. Julian, L. D.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 13813-13822
31. Hoover, J. M.; DiPasquale, A.; Mayer, J. M.; Michael, F. E. J. Am. Chem. Soc. 2010, 132, 5043-5053
32. Xu, H.-C.; Moeller, K. D. J. Am. Chem. Soc. 2010, 132, 2839-2844
33. Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z. J. Am. Chem. Soc. 1988, 110, 3994-4002
34. Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584-3585
35. Bowie, A. L., Jr.; Trauner, D. J. Org. Chem. 2009, 74, 1581-1586
36. Yip, K.-T.; Li, J.-H.; Lee, O.-Y.; Yang, D. Org. Lett. 2005, 7, 5717-5719
37. Baran, P. S.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 7904-7905
38. Brasche, G.; García-Fortanet, J.; Buchwald, S. L. Org. Lett. 2008, 10, 2207-2210
39. McDonald, R. I.; Stahl, S. S. Angew. Chem., Int. Ed. 2010, 49, 5529-5532
40. Diao, T.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 14566-14569
41. 2, see: Bancroft, D. P.; Cotton, F. A.; Verbruggen, M. Acta Crystallogr., Sect. C 1989, 45, 1289-1292
42. Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298-5300
43. van Benthem, R. A. T. M.; Hiemstra, H.; Michels, J. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1994, 357-359
44. Fix, S. R.; Brice, J. L.; Stahl., S. S. Angew. Chem., Int. Ed. 2002, 41, 164-166
45. 2/pyridine catalyst system was first reported for aerobic alcohol oxidation: Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750-6755
46. Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578-9579
47. Trend, R. M.; Ramtohul, Y. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 17778-17788
48. Yip, K.-T.; Yang, M.; Law, K.-L.; Zhu, N.-Y.; Yang, D. J. Am. Chem. Soc. 2006, 128, 3130-3131
49. Rogers, M. M.; Kotov, V.; Chatwichien, J.; Stahl, S. S. Org. Lett. 2007, 9, 4331-4334
50. II-H intermediates is quite common. For a leading reference, see: Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7
51. Chen, M. S.; White, M. C. J. Am. Chem. Soc. 2004, 126, 1346-1347
52. Chen, M. S.; Prabagaran, N.; Labenz, N. A.; White, M. C. J. Am. Chem. Soc. 2005, 127, 6970-6971
53. Fraunhoffer, K. J.; White, M. C. J. Am. Chem. Soc. 2007, 129, 7274-7276
54. Laut, P. B.; Johnstone, D. Chem. Eng. (New York) 1994, 101, 96-104
55. Ye, X.; Johnson, M. D.; Diao, T.; Yates, M. H.; Stahl, S. S. Green Chem. 2010, 12, 1180-1186