Formation of six-membered aza-nickelacycles by oxidative addition of cyclopropyl imines to nickel(0)

Chemistry Letters

Volumn 40, Issue 3, 2011, Pages 248-249

  Tamaki, Takashi ^a   Ohashi, Masato ^a   Ogoshi, Sensuke ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79951864072     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2011.248     Document Type: Article

References (31)

1. M. Murakami, Y. Ito, Top. Organomet. Chem. 1999, 3, 97, and references therein;
2. M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117, and references therein.
3. S. Ogoshi, M. Oka, H. Kurosawa, J. Am. Chem. Soc. 2004, 126, 11802;
4. S. Ogoshi, M. Ueta, T. Arai, H. Kurosawa, J. Am. Chem. Soc. 2005, 127, 12810;
5. S. Ogoshi, K. Tonomori, M. Oka, H. Kurosawa, J. Am. Chem. Soc. 2006, 128, 7077;
6. S. Ogoshi, H. Kamada, H. Kurosawa, Tetrahedron 2006, 62, 7583;
7. S. Ogoshi, H. Ikeda, H. Kurosawa, Angew. Chem., Int. Ed. 2007, 46, 4930;
8. S. Ogoshi, T. Arai, M. Ohashi, H. Kurosawa, Chem. Commun. 2008, 1347;
9. M. Ohashi, O. Kishizaki, H. Ikeda, S. Ogoshi, J. Am. Chem. Soc. 2009, 131, 9160;
10. S. Ogoshi, J. Synth. Org. Chem., Jpn. 2009, 67, 509;
11. S. Ogoshi, A. Nishimura, M. Ohashi, Org. Lett. 2010, 12, 3450.
12. T. Tamaki, M. Nagata, M. Ohashi, S. Ogoshi, Chem.-Eur. J. 2009, 15, 10083.
13. S. Ogoshi, M. Nagata, H. Kurosawa, J. Am. Chem. Soc. 2006, 128, 5350;
14. L. Liu, J. Montgomery, J. Am. Chem. Soc. 2006, 128, 5348;
15. Highlights of the work, see: G. C. Lloyd-Jones, Angew. Chem., Int. Ed. 2006, 45, 6788.
16. Ring-opening reaction of cyclopropyl ketone: T. Ichiyanagi, S. Kuniyama, M. Shimizu, T. Fujisawa, Chem. Lett. 1997, 1149;
17. Y. Sumida, H. Yorimitsu, K. Oshima, J. Org. Chem. 2009, 74, 3196.
18. L.Liu, J. Montgomery, Org. Lett. 2007, 9, 3885.
19. Ring-opening reaction of cyclopropyl imine: P. A. Wender, T. M. Pedersen, M. J. C. Scanio, J. Am. Chem. Soc. 2002, 124, 15154;
20. A. Kamitani, N. Chatani, T. Morimoto, S. Murai, J. Org. Chem. 2000, 65, 9230;
21. T. Kurahashi, A. de Meijere, Synlett 2005, 2619.
22. IPr: 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene: A. J. Arduengo, III, R. Krafczyk, R. Schmutzler, H. A. Craig, J. R. Goerlich, W. J. Marshall, M. Unverzagt, Tetrahedron 1999, 55, 14523.
23. T. Hu, C. Li, Org. Lett. 2005, 7, 2035;
24. I. Ojima, A. Korda, W. R. Shay, J. Org. Chem. 1991, 56, 2024.
25. The treatment of nickel compounds with carbon monoxide can yield Ni(CO)4 (extremely toxic) due to the addition of insufficient amounts of PR3 or IPr, careless handling or an accident. The reaction mixture must be handled in a well-ventilated fume hood.
26. Crystal data for 2a: Mr = 592.50, green, monoclinic, P21/n (No. 14), a = 11.9351(9)Å, b = 19.1441(14)AÅ, c = 15.2179(12)AÅ, β = 107.353(3)°, V = 3318.8(4)AÅ3, Z = 4, Dcalcd = 1.186 g cm-3, T = 150.0°C, R1 = 0.0331 [I > 2·(I)], wR2 = 0.0761 (all data), Crystallographic data reported in this manuscript have been deposited with Cambridge Crystallographic Data Centre as supplementary publication CCDC#: 805799. Copies of the data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB2 1EZ, U.K.; fax: +44 1223 336033; or deposit@ccdc.cam.ac.uk).
27. Montgomery briefly mentioned that the reactivity of N-phenyl imines to enones is comparable to that of N-benzyl imines (ref. 6).
28. After decomposition of six-membered aza-nickelacycle, the corresponding conjugated imine was not observed by the method of 1HNMR and GC-MS analysis (as mentioned ref. 6).
29. Crystal data for 2c: Mr = 587.52, red, tetragonal, P42/n (No. 86), a = 24.7959(10)Å, c = 10.5231(5)Å, V = 6470.0(5)Å3, Z = 8, Dcalcd = 1.206 g cm-3, T = -150.0°C, R1 = 0.0825 [I > 2·(I)], wR2 = 0.2678 (all data). CCDC#: 805800.
30. The respective yields of products were determined by GC analysis.
31. Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.