Unexpected thiol-induced [2 + 2] coupling reaction using a doubly alkynyl bridging diplatinum complex as a precursor

Organometallics

Volumn 17, Issue 9, 1998, Pages 1640-1642

  Berenguer, Jesús R ^a   Forniés, Juan ^b   Lalinde, Elena ^a   Martínez, Francisco ^b   Sánchez, Luis ^b   Serrano, Blanca ^a  

^a UNIVERSITY OF LA RIOJA   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001221866     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om971075n     Document Type: Article

References (59)

1. (1)(a) Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 21.
2. (b) Lotz, S.; Van Rooyen, P. H.; Mayer, R. Adv. Organomet. Chem. 1995, 37, 219.
3. (c) Lang, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 547.
4. (d) Beck, W.; Niemer, B.; Wiesser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923.
5. See for example: (a) Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 969. (b) Bartik, T.; Bartik, B.; Brady, M.; Dembinsky, R.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 414. (c) Le Narvor, N.; Toupet, L.; Lapinte, C. J. Am. Chem. Soc. 1995, 117, 7129. (d) Xia, H. P.; Yeung, R. C. Y.; Jia, G. Organometallics 1997, 16, 3557. (e) Sponsler, M. B. Organometallics 1995, 14, 1920 and references therein, (f) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466.
6. See for example: (a) Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 969. (b) Bartik, T.; Bartik, B.; Brady, M.; Dembinsky, R.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 414. (c) Le Narvor, N.; Toupet, L.; Lapinte, C. J. Am. Chem. Soc. 1995, 117, 7129. (d) Xia, H. P.; Yeung, R. C. Y.; Jia, G. Organometallics 1997, 16, 3557. (e) Sponsler, M. B. Organometallics 1995, 14, 1920 and references therein, (f) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466.
7. See for example: (a) Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 969. (b) Bartik, T.; Bartik, B.; Brady, M.; Dembinsky, R.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 414. (c) Le Narvor, N.; Toupet, L.; Lapinte, C. J. Am. Chem. Soc. 1995, 117, 7129. (d) Xia, H. P.; Yeung, R. C. Y.; Jia, G. Organometallics 1997, 16, 3557. (e) Sponsler, M. B. Organometallics 1995, 14, 1920 and references therein, (f) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466.
8. See for example: (a) Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 969. (b) Bartik, T.; Bartik, B.; Brady, M.; Dembinsky, R.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 414. (c) Le Narvor, N.; Toupet, L.; Lapinte, C. J. Am. Chem. Soc. 1995, 117, 7129. (d) Xia, H. P.; Yeung, R. C. Y.; Jia, G. Organometallics 1997, 16, 3557. (e) Sponsler, M. B. Organometallics 1995, 14, 1920 and references therein, (f) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466.
9. See for example: (a) Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 969. (b) Bartik, T.; Bartik, B.; Brady, M.; Dembinsky, R.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 414. (c) Le Narvor, N.; Toupet, L.; Lapinte, C. J. Am. Chem. Soc. 1995, 117, 7129. (d) Xia, H. P.; Yeung, R. C. Y.; Jia, G. Organometallics 1997, 16, 3557. (e) Sponsler, M. B. Organometallics 1995, 14, 1920 and references therein, (f) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466.
10. See for example: (a) Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 969. (b) Bartik, T.; Bartik, B.; Brady, M.; Dembinsky, R.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 414. (c) Le Narvor, N.; Toupet, L.; Lapinte, C. J. Am. Chem. Soc. 1995, 117, 7129. (d) Xia, H. P.; Yeung, R. C. Y.; Jia, G. Organometallics 1997, 16, 3557. (e) Sponsler, M. B. Organometallics 1995, 14, 1920 and references therein, (f) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466.
11. 5H have also been reported: (a) Shih, K.-Y.; Schrock, R. R.; Kempe, R. J. Am. Chem. Soc. 1994, 116, 8804. (b) Antiñolo, A.; Otero, A.; Fajardo, M.; García-Yebra, C.; Gil-Sanz, R.; Lopez-Mardomingo, C.; Martín, A.; Gómez-Sal, P. Organometállics 1994, 13, 4679. (c) Rappert, T.; Nurnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (d) Jia, G.; Xia, H. P.; Wu, W. F.; Ng, W. S. Organometallics 1996, 15, 3634 and references therein, (e) Jemmis, E. D.; Giju, K. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 606. (f) Rabier, A.; Lugan, N.; Mathieu, R.; Geoffroy, G. L. Organometallics 1994, 13, 4676.
12. 5H have also been reported: (a) Shih, K.-Y.; Schrock, R. R.; Kempe, R. J. Am. Chem. Soc. 1994, 116, 8804. (b) Antiñolo, A.; Otero, A.; Fajardo, M.; García-Yebra, C.; Gil-Sanz, R.; Lopez-Mardomingo, C.; Martín, A.; Gómez-Sal, P. Organometállics 1994, 13, 4679. (c) Rappert, T.; Nurnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (d) Jia, G.; Xia, H. P.; Wu, W. F.; Ng, W. S. Organometallics 1996, 15, 3634 and references therein, (e) Jemmis, E. D.; Giju, K. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 606. (f) Rabier, A.; Lugan, N.; Mathieu, R.; Geoffroy, G. L. Organometallics 1994, 13, 4676.
13. 5H have also been reported: (a) Shih, K.-Y.; Schrock, R. R.; Kempe, R. J. Am. Chem. Soc. 1994, 116, 8804. (b) Antiñolo, A.; Otero, A.; Fajardo, M.; García-Yebra, C.; Gil-Sanz, R.; Lopez-Mardomingo, C.; Martín, A.; Gómez-Sal, P. Organometállics 1994, 13, 4679. (c) Rappert, T.; Nurnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (d) Jia, G.; Xia, H. P.; Wu, W. F.; Ng, W. S. Organometallics 1996, 15, 3634 and references therein, (e) Jemmis, E. D.; Giju, K. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 606. (f) Rabier, A.; Lugan, N.; Mathieu, R.; Geoffroy, G. L. Organometallics 1994, 13, 4676.
14. 5H have also been reported: (a) Shih, K.-Y.; Schrock, R. R.; Kempe, R. J. Am. Chem. Soc. 1994, 116, 8804. (b) Antiñolo, A.; Otero, A.; Fajardo, M.; García-Yebra, C.; Gil-Sanz, R.; Lopez-Mardomingo, C.; Martín, A.; Gómez-Sal, P. Organometállics 1994, 13, 4679. (c) Rappert, T.; Nurnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (d) Jia, G.; Xia, H. P.; Wu, W. F.; Ng, W. S. Organometallics 1996, 15, 3634 and references therein, (e) Jemmis, E. D.; Giju, K. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 606. (f) Rabier, A.; Lugan, N.; Mathieu, R.; Geoffroy, G. L. Organometallics 1994, 13, 4676.
15. 5H have also been reported: (a) Shih, K.-Y.; Schrock, R. R.; Kempe, R. J. Am. Chem. Soc. 1994, 116, 8804. (b) Antiñolo, A.; Otero, A.; Fajardo, M.; García-Yebra, C.; Gil-Sanz, R.; Lopez-Mardomingo, C.; Martín, A.; Gómez-Sal, P. Organometállics 1994, 13, 4679. (c) Rappert, T.; Nurnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (d) Jia, G.; Xia, H. P.; Wu, W. F.; Ng, W. S. Organometallics 1996, 15, 3634 and references therein, (e) Jemmis, E. D.; Giju, K. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 606. (f) Rabier, A.; Lugan, N.; Mathieu, R.; Geoffroy, G. L. Organometallics 1994, 13, 4676.
16. 5H have also been reported: (a) Shih, K.-Y.; Schrock, R. R.; Kempe, R. J. Am. Chem. Soc. 1994, 116, 8804. (b) Antiñolo, A.; Otero, A.; Fajardo, M.; García-Yebra, C.; Gil-Sanz, R.; Lopez-Mardomingo, C.; Martín, A.; Gómez-Sal, P. Organometállics 1994, 13, 4679. (c) Rappert, T.; Nurnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (d) Jia, G.; Xia, H. P.; Wu, W. F.; Ng, W. S. Organometallics 1996, 15, 3634 and references therein, (e) Jemmis, E. D.; Giju, K. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 606. (f) Rabier, A.; Lugan, N.; Mathieu, R.; Geoffroy, G. L. Organometallics 1994, 13, 4676.
17. (a) Fischer, H.; Leroux, F.; Roth, G.; Stumpf, R. Organometallics 1996, 15, 3723.
18. (b) Fischer, H.; Leroux, F.; Stumpf, R.; Roth, G. Chem. Ber. 1996, 129, 1475.
19. (c) Weng, W.; Bartik, T.; Johnson, M. T.; Arif, A. M.; Gladysz, J. A. Organometallics 1995, 14, 889.
20. (d) Boland-Lussier, B. F.; Hughes, R. P. Organometallics 1982, 1, 635.
21. (e) Slovokhotov, Yu. L.; Yanovskyi, A. I.; Andrianov, V. G.; Struchkov, Yu. T. J. Organomet. Chem. 1980, 184, C57.
22. (f) Kolobova, N. Y.; Skripkin, V. V.; Alexandrov, G. G., Struchkov, Yu. T. J. Organomet. Chem. 1979, 169, 293.
23. (g) Davison, A.; Solar, J. P. J. Organomet. Chem. 1978, 155, C8.
24. (h) Bullock, R. M. J. Am. Chem. Soc. 1987, 109, 8087.
25. (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition-Metal Chemistry, 2nd ed.; University Science Books: Mill Valley, CA, 1987.
26. (b) O'Connor, J. M.; Hiibner, K.; Merwin, R.; Gantzel, P. K.; Fong, B. S.; Adams, M.; Rheingold, A. L. J. Am. Chem. Soc. 1997, 119, 3631.
27. (c) Werner, H.; Wiedemann, R.; Steiner, P.; Wolf, J. Chem. Eur. J. 1997, 3, 127.
28. (d) Buil, M. L.; Esteruelas, M. A.; López, A. M.; Oñate, E. Organometallics 1997, 16, 3169.
29. (e) Yang, S.-M.; Chang, M. C-W.; Cheung, K.-K.; Che, C-M.; Peng, S.-M. Organometallics 1997, 16, 2819.
30. (f) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272.
31. (g) Yi, Ch. S.; Liu, N. Organometallics 1996, 15, 3968.
32. (a) Nast, R. Coord. Chem. Rev. 1982, 47, 89.
33. (b) Holton, J.; Lappert, M. F.; Pearce, R.; Yarrow, P. I. W. Chem. Rev. 1983, 83, 135.
34. (c) Bruce, M. I. Pure Appl. Chem. 1986, 58, 553.
35. (d) Bruce, M. I. Pure Appl. Chem. 1990, 6, 1021.
36. (e) Sappa, E.; Tiripicchio, A.; Braunstein, P. Chem. Rev. 1983, 83, 203.
37. (f) Akita, M.; Moro-Oka, Y. Bull. Chem. Soc. Jpn. 1995, 68, 420.
38. (g) Forniés, J.; Lalinde, E. J. Chem. Soc., Dalton Trans. 1996, 2587.
39. (h) Bruce, M. I. Chem. Rev. 1991, 91, 197.
40. (i) Doherty, S.; Corrigan, J. F.; Carty, A. J.; Sappa, E. Adv. Organomet. Chem. 1995, 37, 39.
41. (j) Amouri, H. E.; Gruselle, M. Chem. Rev. 1996, 96, 1077.
42. (k) Werner, H. J. Chem. Soc., Chem. Commun. 1997, 903.
43. Berenguer, J. R.; Forniés, J.; Martinez, F.; Cubero, J. C.; Lalinde, E.; Moreno, M. T.; Welch, A. J. Polyhedron 1993, 12, 1797.
44. (a) Seyferth, D.; Hoke, J. B.; Wheeler, D. R. J. Organomet. Chem. 1988, 341, 421.
45. (b) Cherkas, A. A.; Randall, L. H.; Taylor, N. J.; Mott, G. N.; Yule, J. E.; Guinamant, J. L.; Carty, A. J. Organometallics 1990, 9, 1677 and references therein.
46. (c) Rosenberger, C.; Steunou, N.; Jeannin, S.; Jeannin, Y. J. Organomet. Chem. 1995, 494, 17.
47. + (9%). These data are thought to be due to the presence of an equimolecular mixture of RR/SS and RS/ SR diastereomers. As in the RS/SR isomers there is not any symmetry element which related the two platinum fragments, the expected two different sets of signals must be coincident.
48. + (7%).
49. + (3%).
50. 3)MeOH). MS (FAB+): molecular peak was not observed. The assignments of methylene carbon signals have been confirmed by a DEPT experiment.
51. 18 All non-hydrogen atoms were assigned anisotropic displacement parameters and refined without positional restraints. Hydrogen atoms were not included in the structural model (R1 = 0.0515; wR2 = 0.1467; GOF = 1.048). The highest peak on the final difference Fourier map corresponds to 2.5 e/3 (hole = -2.5).
52. (a) Ogawa, A.; Takeba, M.; Kawakami, J.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1995, 117, 7564.
53. (b) Bäckvall, J. E.; Ericsson, A. J. Org. Chem. 1994, 59, 5850.
54. (a) Peng, J. J.; Peng, S.-M.; Lee, G. H.; Chi, Y. Organometallics 1995, 14, 626.
55. (b) Wu, H.-L.; Lu, G.-L.; Chi, Y.; Farrugia, L. J.; Peng, S.-M.; Lee, G.-H. Inorg. Chem. 1996, 35, 6015.
56. (c) Adams, C. J.; Bruce, M. I.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1993, 452, 121.
57. Frühauf, H.-W. Chem. Rev. 1997, 97, 523.
58. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Open, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1.
59. Sheldrick, G. M. SHELX-93: FORTRAN77 Program for the Refinement of Crystal Structures from Diffraction Data. J. Appl. Crystallogr., manuscript in preparation.