Synthesis of rhazinilam through intramolecular arylcyanation of alkenes catalyzed cooperatively by nickel/aluminum

Tetrahedron

Volumn 71, Issue 26-27, 2015, Pages 4413-4417

  Yamada, Yuuya ^a   Ebata, Shiro ^a   Hiyama, Tamejiro ^a,b   Nakao, Yoshiaki ^a  

^a KYOTO UNIVERSITY   (Japan)

^b CHUO UNIVERSITY   (Japan)

Author keywords

Aluminum; C C bond activation; Carbocyanation; Nickel; Rhazinilam

Indexed keywords

ALKALOID; ALKENE; ALUMINUM; CYANIDE; LACTAM; NICKEL; RHAZINILAM; TUBULIN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ARYLCYANATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; DECARBOXYLATION; DRUG SYNTHESIS; HIGH TEMPERATURE; HYDROLYSIS; IODINATION; PRIORITY JOURNAL; REACTION TIME; SUBSTITUTION REACTION; SUZUKI REACTION;

EID: 84930084835     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.03.012     Document Type: Article

References (35)

1. C.-H. Jun Chem. Soc. Rev. 33 2004 610
2. T. Kondo, and T.-a. Mitsudo Chem. Lett. 34 2005 1462
3. M. Murakami, and T. Matsuda Chem. Commun. 2011 1100
4. C-C Bond Activation G. Dong Topics in Current Chemistry Vol. 346 2014 Springer Berlin, Germany
5. F. Chen, T. Wang, and N. Jiao Chem. Rev. 114 2014 8613
6. Y. Nakao, S. Ebata, A. Yada, T. Hiyama, M. Ikawa, and S. Ogoshi J. Am. Chem. Soc. 130 2008 12874
7. T. Xu, and G. Dong Angew. Chem., Int. Ed. 53 2014 10733
8. L. McMurray, F. O'Hara, and M.J. Gaunt Chem. Soc. Rev. 40 2011 1885
9. W.R. Gutekunst, and P.S. Baran Chem. Soc. Rev. 40 2011 1976
10. J. Yamaguchi, A.D. Yamaguchi, and K. Itami Angew. Chem., Int. Ed. 51 2012 8960
11. M. Tobisu, and N. Chatani Chem. Soc. Rev. 37 2008 300
12. Y. Nakao Top. Curr. Chem. 346 2014 33
13. Y. Nakao Bull. Chem. Soc. Jpn. 85 2012 731
14. Y. Hirata, T. Yukawa, N. Kashihara, Y. Nakao, and T. Hiyama J. Am. Chem. Soc. 131 2009 10964
15. M.P. Watson, and E.N. Jacobsen J. Am. Chem. Soc. 130 2008 12594
16. J.-C. Hsieh, S. Ebata, Y. Nakao, and T. Hiyama Synlett 2010 1709
17. H.H.A. Linde Helv. Chim. Acta 48 1965 1822
18. D.J. Abraham, R.D. Rosenstein, R.L. Lyon, and H.H.S. Fong Tetrahedron Lett. 13 1972 909
19. O. Baoudoin, D. Guenard, and F. Gueritte Mini-Rev. Org. Chem. 1 2004 333
20. A.H. Ratcliffe, G.F. Smith, and G.N. Smith Tetrahedron Lett. 14 1973 5179
21. J.A. Johnson, and D. Sames J. Am. Chem. Soc. 122 2000 6321
22. P. Magnus, and T. Rainey Tetrahedron 57 2001 8647
23. J.A. Johnson, N. Li, and D. Sames J. Am. Chem. Soc. 124 2002 6900
24. A.L. Bowie Jr., C.C. Hughes, and D. Trauner Org. Lett. 7 2005 5207
25. Z. Liu, A.S. Wasmuth, and S.G. Nelson J. Am. Chem. Soc. 128 2006 10352
26. M.G. Banwell, D.A.S. Beck, and A.C. Willis ARKIVOC 2006 163
27. Z. Gu, and A. Zakarian Org. Lett. 12 2010 4224
28. L. McMurray, E.M. Beck, and M.J. Gaunt Angew. Chem., Int. Ed. 51 2012 9288
29. K. Sugimoto, K. Toyoshima, S. Nonaka, K. Kotaki, H. Ueda, and H. Tokuyama Angew. Chem., Int. Ed. 52 2013 7168
30. M.G. Banwell, A.J. Edwards, K.A. Jolliffe, J.A. Smith, E. Hamel, and P. Verdier-Pinard Org. Biomol. Chem. 1 2003 296
31. A.L. Bowie Jr., and D. Trauner J. Org. Chem. 74 2009 1581
32. X. Sui, R. Zhu, G. Li, X. Ma, and Z. Gu J. Am. Chem. Soc. 135 2013 9318
33. E.M. Beck, R. Hatley, and M.J. Gaunt Angew. Chem., Int. Ed. 47 2008 3004
34. C. Schmuck, V. Bickert, M. Merschky, L. Geiger, D. Rupprecht, J. Dudaczek, P. Wich, T. Rehm, and U. Machon Eur. J. Org. Chem. 2008 324
35. A.B. Pangborn, M.A. Giardello, R.H. Grubbs, R.K. Rosen, and F.J. Timmers Organometallics 15 1996 1518