A cationic diruthenium amidinate, [(η5-C5Me 5)Ru(μ2-i-PrN=C(Me)Ni-Pr)Ru(η5-C 5Me5)]+, as an efficient catalyst for the atom-transfer radical reactions

Chemistry Letters

Volumn 33, Issue 4, 2004, Pages 442-443

  Motoyama, Yukihiro ^a   Gondo, Mitsuru ^a   Masuda, Satoshi ^a   Iwashita, Yuya ^a   Nagashima, Hideo ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; ALLYL COMPOUND; ANION; CATION; DIRUTHENIUM AMIDINATE; METAL; NICKEL; PRASEODYMIUM; RUTHENIUM DERIVATIVE; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 3142677417     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.442     Document Type: Article

References (22)

1. Reviews: a) D. P. Curran, in "Comprehensive Organic Synthesis," ed. by B. M. Trost and I. Fleming, Pergamon, Oxford (1991), Vol. 4, p 715. b) J. Iqbal, B. Bhatla, and N. K. Nayyar, Chem. Rev., 94, 519 (1994). c) K. Matyjaszewski and J. Xia, Chem. Rev., 101, 2921 (2001). d) M. Kamigaito, T. Ando, and M. Sawamoto, Chem. Rev., 101, 3689 (2001). e) "Radicals in Organic Synthesis," ed. by P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim (2001). f) A. J. Clark, Chem. Soc. Rev., 31, 1 (2002).
2. Reviews: a) D. P. Curran, in "Comprehensive Organic Synthesis," ed. by B. M. Trost and I. Fleming, Pergamon, Oxford (1991), Vol. 4, p 715. b) J. Iqbal, B. Bhatla, and N. K. Nayyar, Chem. Rev., 94, 519 (1994). c) K. Matyjaszewski and J. Xia, Chem. Rev., 101, 2921 (2001). d) M. Kamigaito, T. Ando, and M. Sawamoto, Chem. Rev., 101, 3689 (2001). e) "Radicals in Organic Synthesis," ed. by P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim (2001). f) A. J. Clark, Chem. Soc. Rev., 31, 1 (2002).
3. Reviews: a) D. P. Curran, in "Comprehensive Organic Synthesis," ed. by B. M. Trost and I. Fleming, Pergamon, Oxford (1991), Vol. 4, p 715. b) J. Iqbal, B. Bhatla, and N. K. Nayyar, Chem. Rev., 94, 519 (1994). c) K. Matyjaszewski and J. Xia, Chem. Rev., 101, 2921 (2001). d) M. Kamigaito, T. Ando, and M. Sawamoto, Chem. Rev., 101, 3689 (2001). e) "Radicals in Organic Synthesis," ed. by P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim (2001). f) A. J. Clark, Chem. Soc. Rev., 31, 1 (2002).
4. Reviews: a) D. P. Curran, in "Comprehensive Organic Synthesis," ed. by B. M. Trost and I. Fleming, Pergamon, Oxford (1991), Vol. 4, p 715. b) J. Iqbal, B. Bhatla, and N. K. Nayyar, Chem. Rev., 94, 519 (1994). c) K. Matyjaszewski and J. Xia, Chem. Rev., 101, 2921 (2001). d) M. Kamigaito, T. Ando, and M. Sawamoto, Chem. Rev., 101, 3689 (2001). e) "Radicals in Organic Synthesis," ed. by P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim (2001). f) A. J. Clark, Chem. Soc. Rev., 31, 1 (2002).
5. Reviews: a) D. P. Curran, in "Comprehensive Organic Synthesis," ed. by B. M. Trost and I. Fleming, Pergamon, Oxford (1991), Vol. 4, p 715. b) J. Iqbal, B. Bhatla, and N. K. Nayyar, Chem. Rev., 94, 519 (1994). c) K. Matyjaszewski and J. Xia, Chem. Rev., 101, 2921 (2001). d) M. Kamigaito, T. Ando, and M. Sawamoto, Chem. Rev., 101, 3689 (2001). e) "Radicals in Organic Synthesis," ed. by P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim (2001). f) A. J. Clark, Chem. Soc. Rev., 31, 1 (2002).
6. Reviews: a) D. P. Curran, in "Comprehensive Organic Synthesis," ed. by B. M. Trost and I. Fleming, Pergamon, Oxford (1991), Vol. 4, p 715. b) J. Iqbal, B. Bhatla, and N. K. Nayyar, Chem. Rev., 94, 519 (1994). c) K. Matyjaszewski and J. Xia, Chem. Rev., 101, 2921 (2001). d) M. Kamigaito, T. Ando, and M. Sawamoto, Chem. Rev., 101, 3689 (2001). e) "Radicals in Organic Synthesis," ed. by P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim (2001). f) A. J. Clark, Chem. Soc. Rev., 31, 1 (2002).
7. a) H. Nagashima, H. Wakamatsu, K. Ito, Y. Tomo, and J. Tsuji, Tetrahedron Lett., 23, 2395 (1983).
8. b) H. Nagashima, H. Wakamatsu, and K. Itoh, J. Chem. Soc., Chem. Commun., 1984, 652.
9. c) H. Nagashima, N. Ozaki, M. Ishii, K. Seki, M. Washiyama, and K. Itoh, J. Org. Chem., 58, 464 (1993).
10. a) Y. Yamaguchi and H. Nagashima, Organometallics, 19, 725 (2000).
11. b) H. Kondo, A. Kageyama, Y. Yamaguchi, M. Haga, K. Kirchner, and H. Nagashima, Bull. Chem. Soc. Jpn., 74, 1927 (2001).
12. c) H. Nagashima, M. Gondo, S. Masuda, H. Kondo, Y. Yamaguchi, and K. Matsubara, Chem. Commun., 2003, 442.
13. Also see: d) H. Nagashima, H. Kondo, T. Hayashida, Y. Yamaguchi, M. Gondo, S. Masuda, K. Miyazaki, K. Matsubara, and K. Kirchner, Coord. Chem. Rev., 245, 177 (2003).
14. a) H. Kondo, Y. Yamaguchi, and H. Nagashima, J. Am. Chem. Soc., 123, 500 (2001).
15. b) H. Kondo, K. Matsubara, and H. Nagashima, J. Am. Chem. Soc., 124, 534 (2002).
16. a) M. A. Rachita and G. A. Slough, Tetrahedron Lett., 34, 6821 (1993).
17. b) A. J. Clark, D. J. Duncalf, R. P. Filik, D. M. Haddleton, G. H. Thomas, and H. Wongtap, Tetrahedron Lett., 40, 3807 (1999).
18. c) A. J. Clark, R. P. Filik, and G. H. Thomas, Tetrahedron Lett., 40, 4885 (1999).
19. d) A. J. Clark, R. P. Filik, D. M. Haddleton, A. Radigue, C. J. Sanders, G. H. Thomas, and M. E. Smith, J. Org. Chem., 64, 8954 (1999).
20. It is known that equilibrium between the trans- and cis-isomers of this type of compounds easily took place in the presence of transition metal complexes over 80°C, and the thermodynamically controlled ratio of trans- to cis-10 reached ca. 4:1: a) G. A. Slough, Tetrahedron Lett., 34, 6825 (1993). b) S. Iwamatsu, H. Kondo, K. Matsubara, and H. Nagashima, Tetrahedron, 55, 1687 (1999).
21. It is known that equilibrium between the trans- and cis-isomers of this type of compounds easily took place in the presence of transition metal complexes over 80°C, and the thermodynamically controlled ratio of trans- to cis-10 reached ca. 4:1: a) G. A. Slough, Tetrahedron Lett., 34, 6825 (1993). b) S. Iwamatsu, H. Kondo, K. Matsubara, and H. Nagashima, Tetrahedron, 55, 1687 (1999).
22. 2 as an eluent) in quantitative yield (Table 1, Entry 9).