Catalytic dicyanative [4+2] cycloaddition triggered by cyanopalladation of conjugated enynes under aerobic conditions

Journal of the American Chemical Society

Volumn 132, Issue 13, 2010, Pages 4522-4523

  Arai, Shigeru ^a   Koike, Yuka ^a   Hada, Hirohiko ^a   Nishida, Atsushi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

[4 + 2] CYCLOADDITION; [4+2] CYCLOADDITION REACTIONS; AEROBIC CONDITION; C-C BONDS; CARBOCYCLES; CONJUGATED ENYNES; CYANATION; CYCLOHEXENE RING; FUNCTIONALIZED; INTERMOLECULAR CYCLOADDITION; METHYL ACRYLATES; REGIO-SELECTIVE; STEREOGENIC CENTERS; TERMINAL ALKYNE; TRIPLE BONDS;

ACETYLENE; CYCLOADDITION; OLEFINS; PALLADIUM; REACTION INTERMEDIATES; REGIOSELECTIVITY;

CYCLIZATION;

CARBON; CYCLOHEXENE DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL BOND; CYCLIZATION; CYCLOADDITION; STEREOCHEMISTRY;

ALKYNES; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; NITRILES; OXYGEN; STEREOISOMERISM;

EID: 77950823886     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja910451j     Document Type: Article

References (27)

1. Funabiki, T., Yamazaki, Y., and Tarama, K. J. Chem. Soc., Chem. Commun. 1978, 63
2. Fallon, G. D., Fitzmaurice, N. J., Jackson, W. R., and Perlmutter, P. J. Chem. Soc., Chem. Commun. 1985, 4
3. Chatani, N. and Hanafusa, T. J. Chem. Soc., Chem. Commun. 1985, 838
4. Chatani, N., Takeyasu, T., Horiuchi, N., and Hanafusa, T. J. Org. Chem. 1988, 53, 3539
5. Suginome, M., Kinugasa, H., and Ito, Y. Tetrahedron Lett. 1994, 35, 8635
6. Chatani, N., Horiuchi, N., and Hanafusa, T. J. Org. Chem. 1990, 55, 3393
7. Obora, Y., Baleta, A. S., Tokunaga, M., and Tsuji, Y. J. Organomet. Chem. 2002, 660, 173
8. Kamiya, I., Kawakami, J., Yano, S., Nomoto, A., and Ogawa, A. Organometallics 2006, 25, 3562
9. Nakao, Y., Oda, S., and Hiyama, T. J. Am. Chem. Soc. 2004, 126, 13904
10. Nakao, Y., Kanyiva, K. S., Oda, S., and Hiyama, T. J. Am. Chem. Soc. 2006, 128, 8146
11. Cheng, Y., Duan, Z., Zhongxian, Y., Zhu, Y., and Wu, Y. Org. Lett. 2008, 10, 901
12. For acylcyanation, see: Nozaki, K., Sato, N., and Takaya, H. J. Org. Chem. 1994, 59, 2679
13. Kobayashi, Y., Kamisaki, H., Yanada, R., and Takemoto, Y. Org. Lett. 2006, 8, 2711 For olefins
14. Nakao, Y., Ebata, S., Yada, A., Hiyama, T., Ikawa, M., and Ogoshi, S. J. Am. Chem. Soc. 2008, 130, 12874 For a review of recent progress of carbocyanation:
15. Nájera, C. and Sansano, J. M. Angew. Chem., Int. Ed. 2009, 48, 2452
16. Suginome, M., Yamamoto, A., and Murakami, M. J. Am. Chem. Soc. 2003, 125, 6358
17. Suginome, M., Yamamoto, A., and Murakami, M. Angew. Chem., Int. Ed. 2005, 44, 2380
18. Suginome, M., Yamamoto, A., and Murakami, M. J. Organomet. Chem. 2005, 690, 5300
19. Arai, S., Sato, T., Koike, Y., Hayashi, M., and Nishida, A. Angew. Chem., Int. Ed. 2009, 48, 4528
20. Arai, S., Sato, T., and Nishida, A. Adv. Synth. Catal. 2009, 351, 1897
21. Arai, S., Koike, Y., and Nishida, A. Adv. Synth. Catal. 2010, 352, in press (DOI: 10.1002/adsc.200900813). For a review of palladium chemistry. Tsuji, J. Palladium Reagents and Catalysis; Wiley: 2004. For a review of palladium catalysis with oxidants:
22. Tsuji J. Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400
23. Beccalli, E. M., Broggini, G., Martinelli, M., and Sottocornola, S. Chem. Rev. 2007, 107, 5318 Recently, Pd-catalyzed oxidative cyclization of enynes have been reported.
24. Welbes, L. L., Lyons, T. W., Cychosz, K. A., and Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 5836
25. Tsujihara, T., Takenaka, K., Onitsuka, K., Hatanaka, M., and Sasai, H. J. Am. Chem. Soc. 2009, 131, 3452
26. ORTEP figures for both trans-and cis- 2a and additional details of X-ray analysis are in the Supporting Information.
27. Substrates having allene, internal alkyne, and diene moieties instead of alkenes were all unsuccessful in catalytic dicyanative [4+2] cycloaddition, see: Supporting Information.