The first evidence of insertion of isocyanide into a metal-sulfur bond: Catalytic and stoichiometric behavior of isocyanide and thiolate ligands on palladium and platinum

Journal of the American Chemical Society

Volumn 119, Issue 20, 1997, Pages 4669-4677

  Kuniyasu, Hitoshi ^a   Sugoh, Kunihiko ^a   Su, Moon Song ^a   Kurosawa, Hideo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; ISOCYANIC ACID DERIVATIVE; ISOCYANIDE; LIGAND; METAL; PALLADIUM; PLATINUM; SULFUR; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; COMPLEX FORMATION; OXIDATION; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0030988546     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970518b     Document Type: Article

References (66)

1. Koelle, U.; Rietmann, C.; Tjoe, J.; Wagner, T.; Englert, U. Organometallics 1995, 14, 703.
2. Wakatsuki, Y.; Yamazaki, H.; Iwasaki, H. J. Am. Chem. Soc. 1973, 95, 5781.
3. Halbert, T. R.; Pan, W. H.; Stiefel, E. J. Am. Chem. Soc. 1983, 105, 5476.
4. Carlton, L.; Bakar, W. A. W. A.; Davidson, J. L. J. Organomet. Chem. 1990, 394, 177.
5. (a) Kajitani, M.; Hisamatsu, N.; Takehera, M.; Mori, Y.; Sugiyama, T.; Akiyama, T.; Sugimori, A. Chem. Lett. 1994, 473.
6. (b) Davidson, J. L.; Sharp, D. W. A. J. Chem. Soc., Dalton Trans. 1975, 2283.
7. (a) Imhof, W.; Hunttner, G. J. Organomet. Chem. 1993, 447, 31.
8. (b) Petillon, F. Y.; Roch-Perennou, F. L.; Guerchais, J. E. J. Organomet. Chem. 1979, 173, 89.
9. (c) Fässler, T.; Huttner, G. J. Organomet. Chem. 1989, 376, 367.
10. (a) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902.
11. (b) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525.
12. (c) Bäckvall, J. E.; Ericsson, A. J. Org. Chem. 1994, 59, 5850.
13. (d) Dzhemilev, U. M.; Kunakova, R. V.; Gaisin, R. L. Izv. Akad. Nauk SSSR, Ser. Khim. 1981, 11, 2655.
14. (a) Kuniyasu, H.; Ogawa, A.; Miyazaki, S.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 9796.
15. (b) Dzhemilev, U. M.; Kunakova, R. V.; Baibulatova, N. Z.; Mustafina, E. M.; Galkin, E. G.; Tolstikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 3, 747.
16. (c) Ogawa, A.; Takeba, M.; Kawakami, J.; Ryu, L; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1995, 117, 7564.
17. Ishiyama, T.; Nishijima, K.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 7219.
18. Han, L.; Choi, N.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 7000.
19. (a) Antebi, S.; Alper, H. Organomelallics 1986, 5, 596.
20. (b) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609.
21. (c) Shim, S. C.; Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 1935.
22. (d) Takahashi, H.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1987, 334, C43.
23. (d) Wang, M. D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 21.
24. (e) Kim, Y. J.; Osakada, K.; Sugita, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1988, 7, 2182.
25. (f) Liu, H.; Tan, A. L.; Mok, K. F.; Hor, T. S. A. J. Chem. Soc., Dalton Trans. 1996. 4023.
26. (g) Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89.
27. (h) Burgmayer, S. J, N.; Templeton, J. L. Inorg. Chem. 1985, 24, 3939 and references therein.
28. For the utility of 1:m adducts in organic synthesis, see: (a) Alcaide, B.; Dominguez, G.; Plumet. J.; Sierra, M. A. J. Org. Chem. 1992, 57, 447. (b) Reddy, T. I.; Bhawal, B. M.; Rajappa, S. Tetrahedron Lett. 1992, 33, 2857. (c) Ueno, Y.; Nakai, T.; Okawara, M. Bull. Chem. Soc. Jpn. 1971, 44, 1933. (d) Milzner, K.; Seckinger, K. Helv. Chim. Acta 1974, 57, 1614.
29. For the utility of 1:m adducts in organic synthesis, see: (a) Alcaide, B.; Dominguez, G.; Plumet. J.; Sierra, M. A. J. Org. Chem. 1992, 57, 447. (b) Reddy, T. I.; Bhawal, B. M.; Rajappa, S. Tetrahedron Lett. 1992, 33, 2857. (c) Ueno, Y.; Nakai, T.; Okawara, M. Bull. Chem. Soc. Jpn. 1971, 44, 1933. (d) Milzner, K.; Seckinger, K. Helv. Chim. Acta 1974, 57, 1614.
30. For the utility of 1:m adducts in organic synthesis, see: (a) Alcaide, B.; Dominguez, G.; Plumet. J.; Sierra, M. A. J. Org. Chem. 1992, 57, 447. (b) Reddy, T. I.; Bhawal, B. M.; Rajappa, S. Tetrahedron Lett. 1992, 33, 2857. (c) Ueno, Y.; Nakai, T.; Okawara, M. Bull. Chem. Soc. Jpn. 1971, 44, 1933. (d) Milzner, K.; Seckinger, K. Helv. Chim. Acta 1974, 57, 1614.
31. For the utility of 1:m adducts in organic synthesis, see: (a) Alcaide, B.; Dominguez, G.; Plumet. J.; Sierra, M. A. J. Org. Chem. 1992, 57, 447. (b) Reddy, T. I.; Bhawal, B. M.; Rajappa, S. Tetrahedron Lett. 1992, 33, 2857. (c) Ueno, Y.; Nakai, T.; Okawara, M. Bull. Chem. Soc. Jpn. 1971, 44, 1933. (d) Milzner, K.; Seckinger, K. Helv. Chim. Acta 1974, 57, 1614.
32. Saegusa, T.; Ito, Y. Synthesis 1975, 291.
33. The complex 12 was confirmed only in situ because of fast dimerization to 13. The authentic 13, 14, 18, and 19 were synthesized and fully characterized. See the Experimental Section.
34. Zanella, R.; Ros, R.; Graziani, M. Inorg. Chem. 1973, 12, 2736.
35. Baran̄ano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937.
36. 2- (dppe).
37. 4 in the presence of 3 equiv of 2 provided 14 without forming 12 and 13, implying the precedence of coordination of 2 to Pd(0) over the oxidative addition or fast coordination of 2 to 12 in the actual catalytic condition.
38. 4 showed that Pd(0) exclusively reacted with 1 over 3.
39. 2 with RNC, see: Rauchfuss, T. B.; Shu, J. S.; Roundhill, D. M. Inorg. Chem. 1976, 15, 2096.
40. 2 was also produced under more severe reaction conditions, demonstrating that the dimer was also thermodynamically more stable than monomer 18. See the Experimental Section.
41. Pt-P = 2898 Hz vs 2917 Hz), see: (a) Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335. (b) Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th ed.; Wiley: New York, 1988; p 1299.
42. Pt-P = 2898 Hz vs 2917 Hz), see: (a) Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335. (b) Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th ed.; Wiley: New York, 1988; p 1299.
43. 3, so the different reactivities of the metal complexes would not rely on the different geometry of the complexes.
44. Goddard et al. have demonstrated the differences of C-C or C-H reductive elimination between palladium(II) and platinum(II) complexes by ab initio calculation, see: Low, J. J.; Goddard, W. A., III. J. Am. Chem. Soc. 1984, 106, 6928.
45. (a) Clericuzio, M.; Alagona, G.; Ghio, C.; Salvadori, P. J. Am. Chem. Soc. 1997, 119, 1059.
46. (b) Christian, D. F; Clark, H. C.; Stepaniak, R. F. J. Organomet. Chem. 1976, 112, 209.
47. (c) Saegusa, T.; Bobayashi, S.; Hirota, K.; Okumura, Y.; Ito, Y. Bull. Chem. Soc. Jpn. 1968, 41, 1638.
48. For example: (a) Motz, P. L.; Alexander, J. J.; Ho, D. M. Organometallics 1989, 8, 2589. (b) Yamamoto, Y.; Yamazaki, H. Coord. Chem. Rev. 1972, 8, 225 and references therein. (c) Ogawa, H.; Joh, T.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1988, 561. (d) Onitsuka, K.; Yanai, K.; Takei, F.; Joh, T.; Takahashi, S. Organometallics 1994, 13, 3862. (e) Yamamoto, Y.; Yamazaki, H. Inorg. Chem. 1974, 13, 438. (f) Kosugi, M.; Ogata, T.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1986, 1197.
49. For example: (a) Motz, P. L.; Alexander, J. J.; Ho, D. M. Organometallics 1989, 8, 2589. (b) Yamamoto, Y.; Yamazaki, H. Coord. Chem. Rev. 1972, 8, 225 and references therein. (c) Ogawa, H.; Joh, T.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1988, 561. (d) Onitsuka, K.; Yanai, K.; Takei, F.; Joh, T.; Takahashi, S. Organometallics 1994, 13, 3862. (e) Yamamoto, Y.; Yamazaki, H. Inorg. Chem. 1974, 13, 438. (f) Kosugi, M.; Ogata, T.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1986, 1197.
50. For example: (a) Motz, P. L.; Alexander, J. J.; Ho, D. M. Organometallics 1989, 8, 2589. (b) Yamamoto, Y.; Yamazaki, H. Coord. Chem. Rev. 1972, 8, 225 and references therein. (c) Ogawa, H.; Joh, T.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1988, 561. (d) Onitsuka, K.; Yanai, K.; Takei, F.; Joh, T.; Takahashi, S. Organometallics 1994, 13, 3862. (e) Yamamoto, Y.; Yamazaki, H. Inorg. Chem. 1974, 13, 438. (f) Kosugi, M.; Ogata, T.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1986, 1197.
51. For example: (a) Motz, P. L.; Alexander, J. J.; Ho, D. M. Organometallics 1989, 8, 2589. (b) Yamamoto, Y.; Yamazaki, H. Coord. Chem. Rev. 1972, 8, 225 and references therein. (c) Ogawa, H.; Joh, T.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1988, 561. (d) Onitsuka, K.; Yanai, K.; Takei, F.; Joh, T.; Takahashi, S. Organometallics 1994, 13, 3862. (e) Yamamoto, Y.; Yamazaki, H. Inorg. Chem. 1974, 13, 438. (f) Kosugi, M.; Ogata, T.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1986, 1197.
52. For example: (a) Motz, P. L.; Alexander, J. J.; Ho, D. M. Organometallics 1989, 8, 2589. (b) Yamamoto, Y.; Yamazaki, H. Coord. Chem. Rev. 1972, 8, 225 and references therein. (c) Ogawa, H.; Joh, T.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1988, 561. (d) Onitsuka, K.; Yanai, K.; Takei, F.; Joh, T.; Takahashi, S. Organometallics 1994, 13, 3862. (e) Yamamoto, Y.; Yamazaki, H. Inorg. Chem. 1974, 13, 438. (f) Kosugi, M.; Ogata, T.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1986, 1197.
53. For example: (a) Motz, P. L.; Alexander, J. J.; Ho, D. M. Organometallics 1989, 8, 2589. (b) Yamamoto, Y.; Yamazaki, H. Coord. Chem. Rev. 1972, 8, 225 and references therein. (c) Ogawa, H.; Joh, T.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1988, 561. (d) Onitsuka, K.; Yanai, K.; Takei, F.; Joh, T.; Takahashi, S. Organometallics 1994, 13, 3862. (e) Yamamoto, Y.; Yamazaki, H. Inorg. Chem. 1974, 13, 438. (f) Kosugi, M.; Ogata, T.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1986, 1197.
54. (a) Tanase, T.; Ohizumi, T.; Kobayashi, K.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1992, 707.
55. (b) Christian, D. F.; Clark, H. C. J. Organomet. Chem. 1975, 85, C9.
56. (a) Ito, Y.; Suginome, M.; Matsuura, T.; Murakami, M. J. Am. Chem. Soc. 1991, 113, 8899.
57. (b) Ito, Y.; Bando, T.; Matsuura, T.; Ishikawa, M. J. Chem. Suc., Chem. Commun. 1986, 980.
58. (c) Ito, Y.; Ito, I.; Hirao, T.; Saegusa, T. Synth. Commun. 1974, 4, 97.
59. (a) Chisholm, M. H.; Hammond, C. E.; Ho, D., Huffman, J. C. J. An Chem. Soc. 1986, 108, 7860.
60. (b) Dormond, A.; Aaliti, A.; Moïse, C. J. Chem. Soc., Chem. Commun. 1985, 1231.
61. Crociani, B.; Richards, R. L. J. Chem. Soc., Chem. Commun. 1973, 127.
62. (a) Obrecht, R.; Herrmann, R.; Ugi, I. Synthesis 1985, 400.
63. (b) Ugi, I.; Merv, R.; Lipinski, M.; Bodesheim, F.; Rosendahl, F. In Organic Syntheses, Wiley: New York, 1973; Vol. V. p 300.
64. (a) Coulson, D. R. Inorg. Synth. 1972, 13, 121.
65. (b) Ugo, R.; Cariati, F.; Monica, G. L. Inorg. Synth. 1968, 11, 105.
66. Ukai, T.; Kawazura, H.; Isii, Y. J. Organomet. Chem. 1974, 65, 253.