Synthesis and properties of alkylruthenium complexes bearing primary and secondary amine ligands

Journal of Organometallic Chemistry

Volumn 692, Issue 1-3, 2007, Pages 408-419

  Koike, Takashi ^a   Ikariya, Takao ^a  

^a Tokyo Institute of Technology ^*  (Japan)

Author keywords

Alkylruthenium; Alkylzinc reagents; Amido ruthenium complex; Primary amine ligands; Transmetalation

Indexed keywords

AMINES; COMPLEXATION; MOLECULAR STRUCTURE; ORGANOMETALLICS; PROTONS; SYNTHESIS (CHEMICAL);

ALKYL COMPLEXES; ALKYLRUTHENIUM; ALKYLZINC REAGENTS; AMIDO RUTHENIUM COMPLEX; PRIMARY AMINE LIGANDS; TRANSMETALATION;

RUTHENIUM COMPOUNDS;

EID: 33845617274     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2006.04.047     Document Type: Article

References (33)

1. Haack K.-J., Hashiguchi S., Fujii A., Ikariya T., and Noyori R. Angew. Chem., Int. Ed. Engl. 36 (1997) 285
2. Ikariya T., Hashiguchi S., Murata K., and Noyori R. Org. Synth. 82 (2005) 10
3. Watanabe M., Murata K., and Ikariya T. J. Am. Chem. Soc. 125 (2003) 7508
4. Ikariya T., Wang H., Watanabe M., and Murata K. J. Organomet. Chem. 689 (2004) 1377
5. Watanabe M., Ikagawa A., Wang H., Murata K., and Ikariya T. J. Am. Chem. Soc. 126 (2004) 11148
6. Wang H., Watanabe M., and Ikariya T. Tetrahedron Lett. 46 (2005) 963
7. Ikariya T., Murata K., and Noyori R. Org. Biomol. Chem. 4 (2006) 393
8. Fulton J.R., Bouwkamp M.W., and Bergman R.G. J. Am. Chem. Soc. 122 (2000) 8799
9. Jayaprakash K.N., Conner D., and Gunnoe T.B. Organometallics 20 (2001) 5254
10. Murata K., Konishi H., Ito M., and Ikariya T. Organometallics 21 (2002) 253
11. Tobe M.L. Adv. Inorg. Bioinog. Mech. 2 (1983) 1
12. An X-ray crystallographic analysis of 3b was performed in Fig. 1. The crystallographic data and structure refinement parameters of complex 3b is shown in Table 1. All hydrogen atoms were calculated from ideal geometries. See Supporting information.
13. X-ray crystallographic analysis of the chloro(amine) Ru complexes (2a-e) confirmed that they have a three-legged piano stool coordination environment with arene, chloro, sulfonamido, and amine ligands. The chirality of the (S,S)-diamine ligands determines the R configuration around the central metal [1].
14. Morandini F., Consiglio G., and Lucchini V. Organometallics 4 (1985) 1202
15. Consiglio G., Morandini F., Clani G.F., and Sironi A. Organometallics 5 (1986) 1976
16. An X-ray crystallographic analysis of 4b was performed. In Fig. 2, there are omissions of the other molecule of the same structure. Crystallographic data and structure refinement parameters of complex 4b is shown in Table 1. All hydrogen atoms were calculated from ideal geometries. See Supporting information.
17. An X-ray crystallographic analysis of 5d was performed and described in Fig. 3. Crystallographic data and structure refinement parameters of complex 5d is shown in Table 1. All hydrogen atoms were calculated from ideal geometries. See Supporting information.
18. Abdur-Rashid K., Clapham S.E., Hadzovic A., Harvey J.N., Lough A.J., and Morris R.H. J. Am. Chem. Soc. 124 (2002) 15104
19. Koike T., and Ikariya T. Adv. Synth. Catal. 346 (2004) 37
20. w) = 0.070 (0.093) for 35028 observed reflections (I > 3.00σ(I)). All hydrogen atoms were calculated from ideal geometries. See Supporting information.
21. Interconversion between C-bound and N- or O-bound Ru complexes has been reported. Hartwig J.F., Andersen R.A., and Bergman R.G. J. Am. Chem. Soc. 112 (1990) 5670
22. Hartwig J.F., Bergman R.G., and Andersen R.A. Organometallics 10 (1991) 3326
23. Naota T., Tannna A., and Murahashi S.-I. J. Am. Chem. Soc. 122 (2000) 2960
24. Naota T., Tannna A., Kamuro S., and Murahashi S.-I. J. Am. Chem. Soc. 124 (2002) 6842
25. Thermolysis of the other methyl complexes 3a and 3d provided the cyclometalated complexes. Koike T., and Ikariya T. Organometallics 24 (2005) 724
26. Yamamoto A. Organotransition Metal Chemistry: Fundamental Concepts and Applications (1986), John Wiley & Sons, Inc.
27. Ozawa F., Ito T., and Yamamoto A. J. Am. Chem. Soc. 102 (1980) 6457
28. Komiya S., Morimoto Y., Yamamoto A., and Yamamoto T. Organometallics 1 (1982) 1528
29. Hackett M., Ibers J.M., and Whitesides G.M. J. Am. Chem. Soc. 110 (1988) 1436
30. Alibrandi G., Scolaro L.M., Minniti D., and Romeo R. Inorg. Chem. 29 (1990) 3467
31. It was reported that the decomposition of the alkyl complexes proceeds via β-elimination in preference to protonolysis in water. Komiya S., Ikuine M., Komine N., and Hirano M. Bull. Chem. Soc. Jpn. 76 (2003) 183
32. -1.
33. Orsini F. Synthesis (1985) 500