Imido-transfer reactions to carbonyl moiety induced by the reactions of imido-bridged cobaltadithiolene complexes with trivalent phosphorus halides

Journal of Organometallic Chemistry

Volumn 674, Issue 1-2, 2003, Pages 63-72

  Nomura, Mitsushiro ^a   Takayama, Chikako ^a,c   Janairo, Gerardo C ^b   Sugiyama, Toru ^a   Yokoyama, Yasuo ^a   Kajitani, Masatsugu ^a  

^a SOPHIA UNIVERSITY   (Japan)

^b DE LA SALLE UNIVERSITY   (Philippines)

^c UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Amide; Cobaltadithiolene; Imido transfer; Imine; Phosphorus trihalide

Indexed keywords

CARBONYL DERIVATIVE; COBALT COMPLEX; HALIDE; IMINE; PHOSPHORUS DERIVATIVE;

CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL PARAMETERS; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; REVIEW; X RAY DIFFRACTION;

EID: 0038329280     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(03)00213-4     Document Type: Article

References (61)

1. Shrauzer G.N. Acc. Chem. Res. 2 1969 72.
2. McCleverty J.A. Prog. Inorg. Chem. 10 1969 49.
3. Sugimori A. Yuki Gosei Kagaku kyokai Shi 48 1990 788.
4. Kajitani M. Hagino G. Tamada M. Fujita T. Sakurada M. Akiyama T. Sugimori A. J. Am. Chem. Soc. 118 1996 489.
5. Sugimori A. Yanagi K. Hagino G. Tamada M. Kajitani M. Akiyama T. Chem. Lett. 1997 807.
6. Sugimori A. Akiyama T. Kajitani M. Sugiyama T. Bull. Chem. Soc. Jpn. 72 1999 879.
7. Kajitani M. Sakurada M. Dohki K. Suetsugu T. Akiyama T. Sugimori A. J. Chem. Soc. Chem. Commun. 1990 19.
8. Sakurada M. Kajitani M. Dohki K. Akiyama T. Sugimori A. J. Organomet. Chem. 423 1992 144.
9. Kajitani M. Kawakita F. Chikuma E. Sakurada M. Akiyama T. Sugimori A. Chem. Lett. 1995 85.
10. Takayama C. Sakamoto N. Harada T. Kajitani M. Sugiyama T. Akiyama T. Sugimori A. Organometallics 15 1996 5077.
11. Takayama C. Kajitani M. Sugiyama T. Sugimori A. J. Organomet. Chem. 563 1998 161.
12. Kajitani M. Suetsugu T. Wakabayashi R. Igarashi A. Akiyama T. Sugimori A. J. Organomet. Chem. 293 1985 C15.
13. Kajitani M. Hisamatsu N. Takehara M. Mori Y. Sugiyama T. Akiyama T. Sugimori A. Chem. Lett. 1994 473.
14. Kajitani M. Suetsugu T. Takagi T. Akiyama T. Sugimori A. Aoki K. Yamazaki H. J. Organomet. Chem. 487 1995 C8.
15. Kajitani M. Eguchi Y. Abe R. Akiyama T. Sugimori A. Chem. Lett. 1990 359.
16. Kajitani M. Hatano H. Fujita T. Okumachi T. Nagao H. Akiyama T. Sugimori A. J. Organomet. Chem. 430 1992 C64.
17. Kim D.-H. Ko J. Park K. Cho S. Kang S.O. Organometallics 18 1999 2738.
18. Nomura M. Yagisawa T. Takayama C. Sugiyama T. Yokoyama Y. Shimizu K. Sugimori A. Kajitani M. J. Organomet. Chem. 611 2000 376.
19. Feig A.L. Lippard S.J. Chem. Rev. 94 1994 759.
20. Collman J.P. Zhang X. Lee V.J. Uffelman E.S. Brauman J.I. Science 261 1993 1404.
21. Ostovic D. Bruice T.C. Acc. Chem. Res. 25 1992 314.
22. Holm R.H. Chem. Rev. 87 1987 1401.
23. Srinivasan K. Michaud P. Kochi J.K. J. Am. Chem. Soc. 108 1986 2309.
24. Au S.-M. Huang J.-S. Yu W.-Y. Fung W.-H. Che C.-M. J. Am. Chem. Soc. 121 1999 9120.
25. Liang J.-L. Huang J.-S. Yu X.-Q. Zhu N. Che C.-M. Chem. Eur. J. 8 2002 1563.
26. Yamada Y. Yamamoto T. Okawara M. Chem. Lett. 1975 361.
27. For recent reports of metal-catalyzed aziridination with PhI=NTs, see:(a) D.A. Evans, M.M. Faul, M.T. Bilodeau, J. Am. Chem. Soc. 116 (1994) 2742;
28. Z. Li, R. Quan, E.N. Jacobsen, J. Am. Chem. Soc. 117 (1995) 5889;
29. K. Noda, N. Hosoya, R. Irie, Y. Ito, T. Katsuki, Synlett (1993) 469;
30. K.J. O'Connor, S.-J. Wey, C.J. Burrows, Tetrahedron Lett. 33 (1992) 1001;
31. D.A. Evans, K.A. Woerpel, M.M. Hinman, M.M. Faul, J. Am. Chem. Soc. 113 (1991) 726;
32. D.A. Evans, M.M. Faul, M.T. Bilodeau, B.A. Anderson, D.M. Barnes, J. Am. Chem. Soc. 115 (1993) 5328;
33. Z. Li, K.R. Conser, E.N. Jacobsen, J. Am. Chem. Soc. 115 (1993) 5326;
34. W. Zhang, N.H. Lee, E.N. Jacobsen, J. Am. Chem. Soc. 116 (1994) 425;
35. H. Nishikori, T. Katsuki, Tetrahedron Lett. 37 (1996) 9245;
36. R.E. Lowenthal, S. Masamune, Tetrahedron Lett. 32 (1991) 7373;
37. D. Tanner, P.G. Anderson, A. Harden, P. Somfai, Tetrahedron Lett. 35 (1994) 4631;
38. A.M. Harm, J.G. Knight, G. Stemp, Synlett (1996) 677;
39. T.-S. Lai, H.-L. Kwong, C.-M. Che, S.-M. Peng, Chem. Commun. (1997) 2373;
40. R.S. Atkinson, W.T. Gattrell, A.P. Ayscough, T.M. Raynham, Chem. Commun. (1996) 1935;
41. J.-P. Simonato, J. Pécaut, W.R. Scheidt, J.-C. Marchon, Chem. Commun. (1999) 989.
42. For recent reports of metal-catalyzed amidation with PhI=NTs, see: S.-M. Au, J.-S. Huang, C.-M. Che, W.-Y. Yu, J. Org. Chem. 65 (2000)
43. J.-L. Liang, X.-Q. Yu, C.-M. Che, Chem. Commun. (2002) 124;
44. Y. Kohmura, T. Katsuki, Tetrahedron Lett. 42 (2001) 3339.
45. Groves J.T. Takahashi T. J. Am. Chem. Soc. 105 1983 2073.
46. Bois J.D. Hong J. Carreira E.M. Day M.W. J. Am. Chem. Soc. 118 1996 915.
47. Minakata S. Ando T. Nishimura M. Ryu I. Komatsu M. Angew. Chem. Int. Ed. Engl. 37 1998 3392.
48. Harlan E.W. Holm R.H. J. Am. Chem. Soc. 112 1990 186.
49. Nomura M. Takayama C. Janairo G.C. Sugiyama T. Yokoyama Y. Kajitani M. Organometallics 22 2003 195.
50. Layer R.W. Chem. Rev. 63 1963 489.
51. 2 ), 2.44 (s, 3H, Me)
52. Roberts R.M. Edwards M.B. J. Am. Chem. Soc. 72 1950 5537.
53. Ulrich H. Sayigh A.A.R. J. Chem. Soc. 1963 5558.
54. Reetz M.T. Jaeger R. Drewlies R. Hübel M. Angew. Chem. Int. Ed. Engl. 30 1991 103.
55. Boger D.L. Corbett W.L. Curran T.T. Kasper A.M. J. Am. Chem. Soc. 113 1991 1713.
56. Trost B.M. Marrs C. J. Org. Chem. 56 1991 6468.
57. Sisko J. Weinreb S.M. J. Org. Chem. 55 1990 393.
58. Alexander M.D. Anderson R.D. Sisko J. Weinreb S.M. J. Org. Chem. 55 1990 2563.
59. Sisko J. Weinreb S.M. Tetrahedron Lett. 29 1989 3037.
60. Melnick M.D. Freyer A.J. Weinreb S.M. Tetrahedron Lett. 29 1989 3891.
61. Boennemann H. Bogdanovic B. Brijoux W. Transition metal-catalyzed synthesis of heterocyclic compounds Kosak J.R. (Ed.), Catalysis in Organic Reactions 1984 31 62 Marcel Dekker New York.