Atom-transfer radical reactions catalyzed by a coordinatively unsaturated diruthenium amidinate, [(η5-C5Me5) Ru(μ2-i-PrNC(Me)Ni-Pr)Ru(η5-C5Me 5)]+

Tetrahedron

Volumn 61, Issue 43, 2005, Pages 10216-10226

  Motoyama, Yukihiro ^a   Hanada, Shiori ^a   Niibayashi, Shota ^a   Shimamoto, Kazuya ^a   Takaoka, Naoki ^a   Nagashima, Hideo ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Amidinate; Coordinatively unsaturated complex; Polymerization; Radical Cyclization; Ruthenium

Indexed keywords

2 BROMOISOBUTYLATE; ACETAMIDE DERIVATIVE; ALKENE DERIVATIVE; BROMIDE; BUTYLATE; CARBON; CATION; COPOLYMER; DIRUTHENIUM AMIDINATE; GAMMA LACTAM DERIVATIVE; HALIDE; METHACRYLIC ACID METHYL ESTER; POLY(METHYL METHACRYLATE); POLY(TETRAHYDROFURAN); RUTHENIUM DERIVATIVE; SODIUM DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; CATALYSIS; CATALYST; CYCLIZATION; ENVIRONMENTAL TEMPERATURE; HALOGENATION; ISOLATION PROCEDURE; MACROMOLECULE; MOLECULAR WEIGHT; PRIORITY JOURNAL; TEMPERATURE MEASUREMENT;

EID: 25144496096     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.08.037     Document Type: Article

References (65)

1. B. Giese Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds 1986 Pergamon New York
2. D.P. Curran B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 4 1991 Pergamon Oxford 715
3. P. Renaud M.P. Sibi Radicals in Organic Synthesis 2001 Wiley-VCH Weinheim
4. M. Asscher, and D. Vofsi J. Chem. Soc. 1961 2261 1963, 1887, 3921
5. H. Nagashima, H. Wakamatsu, K. Ito, Y. Tomo, and J. Tsuji Tetrahedron Lett. 23 1983 2395
6. H. Nagashima, H. Wakamatsu, and K. Itoh J. Chem. Soc., Chem. Commun. 1984 652
7. H. Nagashima, N. Ozaki, K. Seki, M. Ishii, and K. Itoh J. Org. Chem. 54 1989 4497
8. H. Nagashima, K. Seki, N. Ozaki, H. Wakamatsu, K. Itoh, Y. Tomo, and J. Tsuji J. Org. Chem. 55 1990 985
9. H. Nagashima, N. Ozaki, M. Ishii, K. Seki, M. Washiyama, and K. Itoh J. Org. Chem. 58 1993 464
10. Reviews: (a) J. Iqbal, B. Bhatia, and N.K. Nayyar Chem. Rev. 94 1994 519
11. B. Giese, B. Kopping, T. Gobel, J. Dickhaut, G. Thoma, K.J. Kulicke, and F. Trach Org. React. 48 1996 301
12. A.J. Clark Chem. Soc. Rev. 31 2002 1
13. M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura Macromolecules 28 1995 1721
14. J.S. Wang, and K. Matyjaszewski J. Am. Chem. Soc. 117 1995 5614
15. T.E. Patten, T. Xia, K. Abernathy, and K. Matyjaszewski Science 272 1996 866
16. K. Matyjaszewski Controlled Radical Polymerization ACS Symposium Series 685 1998 American Chemical Society Washington
17. T.E. Patten, and K. Matyjaszewski Adv. Mater. 10 1998 901
18. M. Sawamoto, and M. Kamigaito A.-D. Schlüter Synthesis of Polymers Materials Science and Technology Series 1999 Wiley-VCH Weinheim Chapter 6
19. K. Matyjaszewski, and J. Xia Chem. Rev. 101 2001 2921
20. M. Kamigaito, T. Ando, and M. Sawamoto Chem. Rev. 101 2001 3689
21. F. Minisci Acc. Chem. Res. 8 1975 165
22. J.K. Kochi Organometallic Mechanisms and Catalysis 1978 Academic New York
23. R. Davis, and I.F. Groves J. Chem. Soc., Dalton Trans. 1982 2281
24. Y. Yamaguchi, and H. Nagashima Organometallics 19 2000 725
25. H. Kondo, A. Kageyama, Y. Yamaguchi, M. Haga, K. Kirchner, and H. Nagashima Bull. Chem. Soc. Jpn. 74 2001 1927
26. H. Nagashima, M. Gondo, S. Masuda, H. Kondo, Y. Yamaguchi, and K. Matsubara Chem. Commun. 2003 442
27. 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 2003 177
28. H. Kondo, Y. Yamaguchi, and H. Nagashima J. Am. Chem. Soc. 123 2001 500
29. H. Kondo, K. Matsubara, and H. Nagashima J. Am. Chem. Soc. 124 2002 534
30. Preliminary communication, see: Y. Motoyama, M. Gondo, S. Masuda, Y. Iwashita, and H. Nagashima Chem. Lett. 33 2004 442
31. K. Matyjaszewski ACS Symp. Ser. 685 1998 258
32. J. Terasawa, H. Kondo, T. Matsumoto, K. Kirchner, Y. Motoyama, and H. Nagashima Organometallics 24 2005 2713
33. J.A. Seijas, M.P. Vazquez-Tato, L. Castedo, R.J. Estevez, M. Onega, and M. Ruiz Tetrahedron 48 1992 1637
34. H. Ishibashi, N. Uemura, H. Nakatani, M. Okazaki, T. Sato, N. Nakamura, and M. Ikeda J. Org. Chem. 58 1993 2360
35. W.S. Stewart, and T.H. Siddall III Chem. Rev. 70 1970 517
36. O.A. Gansow, J. Killough, and A.R. Burke J. Am. Chem. Soc. 93 1971 4297
37. D.P. Curran, and J. Tamine J. Org. Chem. 56 1991 2746
38. S. Iwamatsu, K. Matsubara, and H. Nagashima J. Org. Chem. 64 1999 9625
39. H. Nagashima, Y. Isono, and S. Iwamatsu J. Org. Chem. 66 2001 315
40. Gaussian 98 package: Gaussian 98, Revision A.11; Gaussian Inc.: Pittsburgh, PA,USA, 2001.
41. M.A. Rachita, and G.A. Slough Tetrahedron Lett. 34 1993 6821
42. A.J. Clark, D.J. Duncalf, R.P. Filik, D.M. Haddleton, G.H. Thomas, and H. Wongtap Tetrahedron Lett. 40 1999 3807
43. A.J. Clark, R.P. Filik, and G.H. Thomas Tetrahedron Lett. 40 1999 4885
44. 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 1999 8954
45. 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-6g to cis-6g reached ca. 4:1: (a) G.A. Sloigh Tetrahedron Lett. 34 1993 6825
46. S. Iwamatsu, H. Kondo, K. Matsubara, and H. Nagashima Tetrahedron 55 1999 1687
47. DFT calculations (Ref. 15) (B3LYP/6-311++G(2d,p)//B3LYP/6-31G(d) level) of cis-6g and trans-6g were carried out to show that the trans-6g proved to be slightly stable (2.75 kJ/mol) than the cis-isomer.
48. Iron-based catalyst: (a) L. Forti, F. Ghelfi, E. Libertini, U.M. Pagnoni, and E. Soragni Tetrahedron 53 1997 17761
49. (b) Cu/bipyridine catalyst, see Ref. 17b.
50. Y. Watanabe, T. Ando, M. Kamigaito, and M. Sawamoto Macromolecules 34 2001 4370
51. n (1.2 in toluene) at the initial stage (<10% conversion), however, such relationship gradually deviates from the linearity because of the decomposition of the catalyst.
52. T. Ando, M. Kamigaito, and M. Sawamoto Macromolecules 33 2000 2819
53. T. Iura, K. Matsubara, and H. Nagashima The Reports of Advanced Material Study Vol. 14 2000 Kyushu University 119
54. H. Nagashima, A. Suzuki, T. Iura, K. Ryu, and K. Matsubara Organometallics 19 2000 3579
55. Recent representative papers: (a) M. Narita, R. Nomura, and T. Endo Macromolecules 31 1998 2774
56. A. Kajiwara, and K. Matyjaszewski Macromolecules 31 1998 3489
57. Matyjaszewski reported the polymerization of MMA with CuBr/dNbipy [dNbipy=4,4′-di(5-nonyl)-2,2′-bipyridine] using poly(THF)-derived bromopropionate as the initiator, in which the temperature over 90°C (24 h, >97% conversion) was required for the reaction (Ref. 24b).
58. The reason why the conversion of MMA reached over 95% in the polymerization using poly(THF)-derived initiator 9b is not clear at present. We assumed that the polyether moiety of both the initiator 9b and the dormant chain might effectively stabilize the highly reactive diruthenium amidinate 4 with an oxophilic nature.
59. ns; this strongly suggests interaction of the radical species at the polymer end with the metallic species leading to abstraction of the halogen atom from the M-X species by the polymer radical. As a consequence of the first and the second points, other two reactions, ATRA and ATRC, should also be promoted by the redox mechanism not involving the free radical chain process.
60. T. Kashiwagi, T. Kitayama, and E. Masuda Macromolecules 19 1986 2160
61. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; Garcia-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. PATTY: The DIRDIF program system; Technical Report of the Crystallography Laboratory; University of Nijmegen: The Netherlands, 1992.
62. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Gelder, R.; Israel, R.; Smits, J. M. M. DIRDIF99: The DIRDIF-99 program system; Technical Report of the Crystallography Laboratory; University of Nijmegen: The Netherlands, 1999.
63. D.T. Cromer, and J.T. Waber International Tables for X-ray Crystallography Vol. 4 1974 Kynoch Birmingham, England Table 2.2 A
64. CrystalStructure 3.6.0: Crystal Structure Analysis Package, Rigaku and Rigaku/MSC (2000-2004); 9009 New Trails: Dr. The Woodlands TX 77381, USA.
65. D.J. Watkin, C.K. Prout, J.R. Carruthers, and P.W. Betteridge Crystals 1996 Chemical Crystallography Laboratory Oxford, UK