Synthesis and characterization of some cationic η3-propargylpalladium complexes

Bulletin of the Chemical Society of Japan

Volumn 72, Issue 12, 1999, Pages 2687-2692

  Tsutsumi, Ken ^b   Kawase, Tomohiro ^b   Kakiuchi, Kiyomi ^b   Ogoshi, Sensuke ^a   Okada, Yuji ^a   Kurosawa, Hideo ^a  

^a OSAKA UNIVERSITY   (Japan)

^b NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; PALLADIUM;

ARTICLE; BINDING AFFINITY; CATALYSIS; LIGAND BINDING; OXIDATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033459584     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.2687     Document Type: Article

References (41)

1. a) S. Doherty, J. F. Corrigan, A. J. Carty, and E. Sappa, Adv. Organomet. Chem., 37, 39 (1995).
2. b) A. Wojcicki, New. J. Chem., 18, 61 (1994).
3. a) J. Tsuji and T. Mandai, Angew. Chem., Int. Ed. Engl., 34, 2589 (1995).
4. b) J. Tsuji, "Palladium Reagents and Catalysts," Wiley, Chichester (1995), pp. 453-471.
5. c) I. Minami, M. Yuhara, H. Watanabe, and J. Tsuji, J. Organomet. Chem., 334, 225 (1987), and references cited therein.
6. a) C. J. Elsevier, H. Kleijn, K. Ruitenberg, and P. Vermeer, J. Chem. Soc., Chem. Commun., 1983, 1529.
7. b) C. J. Elsevier, H. Kleijn, J. Boersma, and P. Vermeer, Organometallics, 5, 716 (1986).
8. Neutral complexes a) Ru: Y. Wakatsuki, H. Yamazaki, Y. Maruyama, and I. Shimizu, J. Chem. Soc., Chem. Commun., 1991, 261.
9. b) Zr: P. W. Blosser, J. C. Gallucci, and A. Wojcicki, J. Am. Chem. Soc., 115, 2994 (1993).
10. c) Zr: G. Rodriguez and G. C. Bazan, J. Am. Chem. Soc., 119, 343 (1997).
11. d) Mo: C. Carfagna, M. Green, M. F. Mahon, S. Rumble, and C. M. Woolhouse, J. Chem. Soc., Chem. Commun., 1993, 879; C. Carfagna, R. J. Deeth, M. Green, M. F. Mahon, J. M. McInnes, S. Pellegrini, and C. B. Woolhouse, J. Chem. Soc., Dalton Trans., 1995, 3975.
12. d) Mo: C. Carfagna, M. Green, M. F. Mahon, S. Rumble, and C. M. Woolhouse, J. Chem. Soc., Chem. Commun., 1993, 879; C. Carfagna, R. J. Deeth, M. Green, M. F. Mahon, J. M. McInnes, S. Pellegrini, and C. B. Woolhouse, J. Chem. Soc., Dalton Trans., 1995, 3975.
13. e) Pd: K. Tsutsumi, S. Ogoshi, S. Nishiguchi, and H. Kurosawa, J. Am. Chem. Soc., 120, 1938 (1998). Cationic complexes
14. f) Mo: V. V. Krivykh, E. S. Taits, P. V. Petrovskii, Y. T. Struchkov, and A. I. Yanovskii, Mendeleev Commun., 1991, 103.
15. g) W, Re: V. V. Krivykh, Organomet. Chem. USSR (Engl. Transl.), 5, 113 (1992); V. V. Krivykh, Metallorg. Khim., 5, 213 (1992).
16. g) W, Re: V. V. Krivykh, Organomet. Chem. USSR (Engl. Transl.), 5, 113 (1992); V. V. Krivykh, Metallorg. Khim., 5, 213 (1992).
17. h) Re: C. P. Casey and C. S. Yi, J. Am. Chem. Soc., 114, 6597 (1992); C. P. Casey, A. D. Selmeczy, J. R. Nash, C. S. Yi, D. R. Powell, and R. K. Hayashi, J. Am. Chem. Soc., 118, 6698 (1996).
18. h) Re: C. P. Casey and C. S. Yi, J. Am. Chem. Soc., 114, 6597 (1992); C. P. Casey, A. D. Selmeczy, J. R. Nash, C. S. Yi, D. R. Powell, and R. K. Hayashi, J. Am. Chem. Soc., 118, 6698 (1996).
19. i) Pt: T. -M. Huang, J. -T, Chen, G. -H. Lee, and Y. Wang, J. Am. Chem. Soc., 115, 1170 (1993).
20. j) Pt: P. W. Blosser, D. G. Schimpff, J. C. Gallucci, and A. Wojcicki, Organometallics, 12, 1993 (1993).
21. k) Pt: P. J. Stang, C. M. Crittell, and A. M. Arif, Organometallics, 12, 4799 (1993).
22. l) Pd: S. Ogoshi, K. Tsutsumi, and H. Kurosawa, J. Organomet. Chem., 493, C19 (1995).
23. m) Pt, Pd: M. W. Baize, P. W. Blosser, V. Plantevin, D. G. Schimpff, J. C. Gallucci, and A. Wojcicki, Organometallics, 15, 164 (1996).
24. C. -C. Su, J. -T. Chen, G. -H. Lee, and Y. Wang, J. Am. Chem. Soc., 116, 4999 (1994).
25. a) S. Ogoshi, Y. Fukunishi, K. Tsutsumi, and H. Kurosawa, Inorg. Chim. Acta, 265, 9 (1997).
26. b) S. Ogoshi, Y. Fukunishi, K. Tsutsumi, and H. Kurosawa, J. Chem. Soc., Chem. Commun., 1995, 2485.
27. I. MacInnes and J. C. Walton, J. Chem. Soc., Perkin Trans. 2, 1987, 1077.
28. D. R. Coulson, Inorg. Synth., 13, 121 (1972).
29. T. Ukai, H. Kawazura, Y. Ishii, J. J. Bonnett, and J. A. Ibers, J. Organomet. Chem., 65, 253 (1974).
30. J. G. Calzada and J. Hooz, Org. Synth., Coll. Vol. VI, 634 (1988).
31. R. K. Crossland and K. L. Servis, J. Org. Chem., 35, 3195 (1970).
32. 2 via β-elimination reaction.
33. 4m
34. A. Ohsuka, T. Fujimori, T. Hirao, H. Kurosawa, and I. Ikeda, J. Chem. Soc., Chem. Commun., 1993, 1039.
35. J. Powell and B. L. Shaw, J. Chem. Soc., A, 1968, 774.
36. 1H NMR spectrum of 8b two separate set of resonances were observed, which reveals that 8b is a mixture of two diastereotopic isomers (major/minor = 9/5). These isomers are due to restricted rotation around the Pd-Cα axis and similar isomers have been reported in, J. M. A. Wouters, R. A. Klein, C. J. Elsevier, L. Häming, and C. H. Stam, Organometallics, 13, 4586 (1994).
37. a) J. P. Collman, L. S. Hegedus, J. R. Norton, and R. G. Finke, "Principles and Applications of Organotransition Metal Chemistry," University Science Books, Mill Valley, CA (1987), pp. 241-244.
38. b) R. H. Crabtree, "The Organometallic Chemistry of the Transition Metals," 2nd ed, Wiley, New York (1994), pp. 7-8.
39. 3) δ = 1.24 (s, 9H), 5.35 (dd, J = 11.0, 2.2 Hz, 1H), 5.53 (dd, J = 17.6, 2.2 Hz, 1H), 5.79 (dd, J = 17.6, 11.0 Hz, 1H).
40. T.-M. Huang, R.-H. Hsu, C.-S. Yang, J. -T. Chen, G. -H. Lee, and Y. Wang, Organometallics, 13, 3657 (1994).
41. 3-propargylpalladium complex: C. P. Casey, J. R. Nash, C. S. Yi, A. D. Selmeczy, S. Chung, D. R. Powell, and R. K. Hayashi, J. Am. Chem. Soc., 120, 722 (1998).