Synthesis of polycyclic nitrogen heterocycles via alkene aminopalladation/carbopalladation cascade reaction

Organic Letters

Volumn 12, Issue 5, 2010, Pages 1028-1031

  Schultz, Danielle M ^a   Wolfe, John P ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; HETEROCYCLIC COMPOUND; NITROGEN; PALLADIUM; POLYCYCLIC HYDROCARBON;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALKENES; HETEROCYCLIC COMPOUNDS; NITROGEN; PALLADIUM; POLYCYCLIC COMPOUNDS;

EID: 77749289180     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100033s     Document Type: Article

References (24)

1. Reviews: (a) Wolfe, J. P. Eur. J. Org. Chem. 2007, 571.
2. (b) Wolfe, J. P. Synlett 2008, 2913.
3. (a) Lira, R.; Wolfe, J. P. J. Am, Chem. Soc. 2004, 126, 13906.
4. (b) Bertrand, M. B.; Wolfe, J. P. Tetrahedron 2005, 61, 6441.
5. (a) Liu, J.-F.; Jiang, Z.-Y.; Wang, R.-R.; Zheng, Y.-T.; Chen, J.-J.; Zhang, X.-M.; Ma, Y.-B. Org. Lett. 2007, 9, 4.127.
6. (b) Kariba, R. M.; Houghton, P. J.; Yenesew, A. J. Nat. Prod. 2002, 65, 566.
7. (a) Ito, Y.; Nakajo, E.; Natatsuka, M.; Saegusa, T. Tetrahedron Lett. 1983, 24, 2881.
8. (b) Pearson, W. H.; Fang, W.-K. Org. Chem. 2000, 65, 7158.
9. (a) Negishi, E.-i.; Wang, G.; Zhu, G. Top. Organomet. Chem. 2006, 19, 1.
10. (b) Maddaford, S. P.; Andersen, N. G.; Cristofoli, W. A.; Keay, B. A. J. Am. Chem. Soc. 1996, 118, 10766.
11. (c) deMeijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
12. (d) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644.
13. For cascade reactions of enynes that proceed through similar intermediates, see: (a) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421.
14. (b) Meyer, F. E.; Parsons, P. J.; de Meijere, A. J. Org. Chem. 1991, 56, 6487,
15. 2 ., alkene complexes followed by alkene carbopalladation, see: Yip, K.-T.; Zhu, N.-Y.; Yang, D. Org. Lett. 2009, 11, 1911, and references cited therein.
16. To the best of our knowledge, only two reports of intermolecular cascade Heck reactions between aryl or alkenyl halides and l,n-dienes have appeared in the literature. In these cases, the transformations were terminated by aryl C-H activation followed by C-C bond formation; all alkene insertion steps proceed through R-Pd-X intermediates. See:
17. (a) Hu, Y.; Ouyang, Y.; Qu, Y.; Hu, Q.; Yao, H. Chem. Commun. 2009, 4575.
18. (b) Hu, Y.; Song, F.; Wu, F.; Cheng, D.; Wang, S. Chem.-Eur. J. 2008, 14, 3110.
19. Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc 2001, 123, 1232.
20. The formation of N-(prop-l-enyl)-2-methylindoli.ne was observed in some instances. The origin of this side product is not entirely clear, but it may result from reduction, or protonolysis of intermediate 3b.
21. (a) Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc 2004, 126, 7460.
22. (b) Kesharwani, T.; Verma, A. K.; Emrich, D.; Ward, J. A.; Larock, R. C. Org. Lett. 2009, 11, 2591, and references cited therein,
23. (c) Ma, S.; Gu, Z. Angew. Chem., Int. Ed. 2005, 44, 7512.
24. For rare examples of 1,5-Pd migration of alkylpalladium intermediates, which occur under oxidative conditions, see: Heumann, A.; Bäckvall, J. E. Angew. Chem., Int. Ed. Engl. 1985, 24, 207.