Palladium(II)-catalyzed intramolecular hydroamination of 1,3-dienes to give homoallylic amines

Angewandte Chemie - International Edition

Volumn 52, Issue 50, 2013, Pages 13311-13313

  Pierson, Justin M ^a   Ingalls, Erica L ^a   Vo, Richard D ^a   Michael, Forrest E ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

1,3 dienes; homoallylic amines; hydroamination; nitrogen heterocycles; palladium catalysis

Indexed keywords

1 ,3-DIENES; HOMOALLYLIC AMINES; HYDROAMINATIONS; NITROGEN HETEROCYCLES; PALLADIUM CATALYSIS;

AMINATION; AMINES; CATALYSIS; PALLADIUM COMPOUNDS;

OLEFINS;

ALKADIENE; ALLYL COMPOUND; AMINE; ORGANOMETALLIC COMPOUND; PALLADIUM;

1,3-DIENES; AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HOMOALLYLIC AMINES; HYDROAMINATION; NITROGEN HETEROCYCLES; PALLADIUM CATALYSIS; SYNTHESIS;

1,3-DIENES; HOMOALLYLIC AMINES; HYDROAMINATION; NITROGEN HETEROCYCLES; PALLADIUM CATALYSIS;

ALKADIENES; ALLYL COMPOUNDS; AMINATION; AMINES; CATALYSIS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 84889677350     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201305766     Document Type: Article

References (29)

1. D. O'Hagan, Nat. Prod. Rep. 2000, 17, 435-446
2. J. R. Liddell, Nat. Prod. Rep. 2002, 19, 773-781.
3. T. E. Müller, K. C. Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev. 2008, 108, 3795-3892.
4. X. Giner, C. Nájera, Org. Lett. 2008, 10, 2919-2922
5. C. Brouwer, C. He, Angew. Chem. 2006, 118, 1776-1779
6. Angew. Chem. Int. Ed. 2006, 45, 1744-1747
7. N. T. Patil, L. M. Lutete, H. Wu, N. K. Pahadi, I. D. Gridnew, Y. Yamamoto, J. Org. Chem. 2006, 71, 4270-4279
8. H. Yamamoto, S. Shiomi, D. Odate, I. Sasaki, K. Namba, H. Imagawa, M. Nishizawa, Chem. Lett. 2010, 39, 830-831.
9. R. W. Armbruster, M. M. Morgan, J. L. Schmidt, C. M. Lau, R. M. Riley, D. L. Zabrowski, H. A. Dieck, Organometallics 1986, 5, 234-237
10. O. Löber, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2001, 123, 4366-4367
11. T. Minami, H. Okamoto, S. Ikeda, R. Tanaka, F. Ozawa, M. Yoshifuji, Angew. Chem. 2001, 113, 4633-4635
12. Angew. Chem. Int. Ed. 2001, 40, 4501-4503
13. J. Pawlas, Y. Nakao, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 3669-3679
14. A. M. Johns, M. Utsunomiya, C. D. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 1828-1839
15. N. Sakai, A. Ridder, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 8134-8135
16. A. M. Johns, Z. Liu, J. F. Hartwig, Angew. Chem. 2007, 119, 7397-7399
17. Angew. Chem. Int. Ed. 2007, 46, 7259-7261.
18. O. Kanno, W. Kuriyama, J. Z. Wang, D. F. Toste, Angew. Chem. 2011, 123, 10093-10096
19. Angew. Chem. Int. Ed. 2011, 50, 9919-9922
20. C. Brinkmann, A. G. M. Barrett, M. S. Hill, P. A. Procopiou, J. Am. Chem. Soc. 2012, 134, 2193-2207.
21. Z. Li, J. Zhang, C. Brouwer, C. G. Yang, N. W. Reich, C. He, Org. Lett. 2006, 8, 4175-4178
22. N. D. Shapiro, V. Rauniyar, G. L. Hamilton, J. Wu, F. D. Toste, Nature 2011, 470, 245-250.
23. S. Hong, T. J. Marks, J. Am. Chem. Soc. 2002, 124, 7886-7887
24. B. D. Stubbert, T. J. Marks, J. Am. Chem. Soc. 2007, 129, 4253-4271.
25. H. Yamamoto, I. Sasaki, S. Shiomi, N. Yamasaki, H. Imagawa, Org. Lett. 2012, 14, 2266-2269.
26. F. E. Michael, B. M. Cochran, J. Am. Chem. Soc. 2006, 128, 4246-4247
27. B. M. Cochran, F. E. Michael, Org. Lett. 2008, 10, 329-332
28. B. M. Cochran, F. E. Michael, J. Am. Chem. Soc. 2008, 130, 2786-2792.
29. L. Barloy, S. Ramdeehul, J. A. Osborn, C. Carlotti, F. Taulelle, A. DeCian, J. Fisher, Eur. J. Inorg. Chem. 2000, 2523-2532.