Pincer "hemilabile" effect. PCN platinum(II) complexes with different amine "arm length"

Organometallics

Volumn 24, Issue 6, 2005, Pages 1082-1090

  Poverenov, Elena ^a   Gandelman, Mark ^a   Shimon, Linda J W ^a   Rozenberg, Haim ^a   Ben David, Yehoshoa ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINES; CATALYSIS; CHEMICAL BONDS; CHEMICAL REACTIONS; COMPLEXATION; ORGANIC ACIDS; ORGANOMETALLICS; POSITIVE IONS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

CARBONYL COMPLEXES; CHLORIDE COMPLEXES; DIAZO COMPOUNDS; LIGANDS;

PLATINUM COMPOUNDS;

EID: 15944383405     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049182m     Document Type: Article

References (40)

1. Recent reviews: (a) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750. (b) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759. (c) (g) Jengen, C. J. Chem. Commun. 1999, 2443. (d) Singleton, J. T. Tetrahedron 2003, 59, 1837. (e) Vigalok, A.; Milstein, D. Acc. Chem. Res. 2001, 34, 798. (f) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870. (g) Milstein, D. Pure Appl. Chem. 2003, 75, 2003. (h) Milstein, D.; Rybtchinski, B. ACS Symp. Ser. 2004, 885, 70.
2. Recent reviews: (a) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750. (b) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759. (c) (g) Jengen, C. J. Chem. Commun. 1999, 2443. (d) Singleton, J. T. Tetrahedron 2003, 59, 1837. (e) Vigalok, A.; Milstein, D. Acc. Chem. Res. 2001, 34, 798. (f) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870. (g) Milstein, D. Pure Appl. Chem. 2003, 75, 2003. (h) Milstein, D.; Rybtchinski, B. ACS Symp. Ser. 2004, 885, 70.
3. Recent reviews: (a) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750. (b) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759. (c) (g) Jengen, C. J. Chem. Commun. 1999, 2443. (d) Singleton, J. T. Tetrahedron 2003, 59, 1837. (e) Vigalok, A.; Milstein, D. Acc. Chem. Res. 2001, 34, 798. (f) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870. (g) Milstein, D. Pure Appl. Chem. 2003, 75, 2003. (h) Milstein, D.; Rybtchinski, B. ACS Symp. Ser. 2004, 885, 70.
4. Recent reviews: (a) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750. (b) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759. (c) (g) Jengen, C. J. Chem. Commun. 1999, 2443. (d) Singleton, J. T. Tetrahedron 2003, 59, 1837. (e) Vigalok, A.; Milstein, D. Acc. Chem. Res. 2001, 34, 798. (f) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870. (g) Milstein, D. Pure Appl. Chem. 2003, 75, 2003. (h) Milstein, D.; Rybtchinski, B. ACS Symp. Ser. 2004, 885, 70.
5. Recent reviews: (a) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750. (b) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759. (c) (g) Jengen, C. J. Chem. Commun. 1999, 2443. (d) Singleton, J. T. Tetrahedron 2003, 59, 1837. (e) Vigalok, A.; Milstein, D. Acc. Chem. Res. 2001, 34, 798. (f) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870. (g) Milstein, D. Pure Appl. Chem. 2003, 75, 2003. (h) Milstein, D.; Rybtchinski, B. ACS Symp. Ser. 2004, 885, 70.
6. Recent reviews: (a) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750. (b) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759. (c) (g) Jengen, C. J. Chem. Commun. 1999, 2443. (d) Singleton, J. T. Tetrahedron 2003, 59, 1837. (e) Vigalok, A.; Milstein, D. Acc. Chem. Res. 2001, 34, 798. (f) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870. (g) Milstein, D. Pure Appl. Chem. 2003, 75, 2003. (h) Milstein, D.; Rybtchinski, B. ACS Symp. Ser. 2004, 885, 70.
7. Recent reviews: (a) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750. (b) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759. (c) (g) Jengen, C. J. Chem. Commun. 1999, 2443. (d) Singleton, J. T. Tetrahedron 2003, 59, 1837. (e) Vigalok, A.; Milstein, D. Acc. Chem. Res. 2001, 34, 798. (f) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870. (g) Milstein, D. Pure Appl. Chem. 2003, 75, 2003. (h) Milstein, D.; Rybtchinski, B. ACS Symp. Ser. 2004, 885, 70.
8. Recent reviews: (a) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750. (b) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759. (c) (g) Jengen, C. J. Chem. Commun. 1999, 2443. (d) Singleton, J. T. Tetrahedron 2003, 59, 1837. (e) Vigalok, A.; Milstein, D. Acc. Chem. Res. 2001, 34, 798. (f) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 870. (g) Milstein, D. Pure Appl. Chem. 2003, 75, 2003. (h) Milstein, D.; Rybtchinski, B. ACS Symp. Ser. 2004, 885, 70.
9. (a) van Koten, G. Pure Appl. Chem. 1989, 62, 1681.
10. (c) Grove, D. M.; van Koten, G.; Verechuuren, A. H. M. J. Mol. Catal. 1988, 45, 169.
11. (d) van Beek, J. A. M.; van Koten, G.; Smeeta, W. J. J.; Spek, A. L. J. Am. Chem. Soc. 1986, 108, 5010.
12. (a) Gandelman, M.; Vigalok, A.; Shimon, L. J. W.; Milstein, D. Organometallics, 1997, 16, 3981.
13. (b) Gandelman, M.; Shimon, L.; Milstein, D. Chem. Eur. J. 2003, 9, 4295.
14. Gandelman, M.; Milstein, D. Chem. Commun. 2000, 1603.
15. Rybtchinski, B.; Cohen, R.; Gandelman, M.; Shimon. L. J. W.; Martin, J. M. I.; Milstein, D. Angew. Chem., Int. Ed. 2003, 115, 1993.
16. (a) Gandelman, M.; Rybtchinski, B.; Ashkenazi, N.; Gauvin, R.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 5372.
17. (b) Cohen, R.; Rybtchinski, B.; Gandelman, M.; Rozenberg, M.; Martin, J. M. L.; Milstein, D. J. Am. Chem. Soc. 2003, 125, 6532.
18. Gandelman, M.; Konstantinovski, L.; Rozenberg, H.; Milstein, D. Chem. Eur. J. 2003, 9, 2595.
19. Gandelman, M.; Vigalok, A.; Kontantinovski, L.; Milstein, D. J. Am. Chem. Soc. 2000, 122, 9848.
20. Rybtchinski, B.; Oevers, S.; Montag, M.; Vigalok, A.; Rogenberg, H.; Martin, J. M. L.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 9064.
21. Crabtree, R. H. The Organometallic Chemistry of The Transition Metals; John Wiley & Sons: New York, 1994.
22. Poverenov, E.; Gandelman, M.; Shimon, L. J. W.; Rozenberg, H.; Ben-David, Y.; Milstein, D. Chem. Eur. J. 2004, 10, 4673.
23. O'Hanlon, P. J.; Rogers, N. H. Eur. Pat. Appl. AN 406065, 1982.
24. (a) Fulton, J. R.; Holland, A. W.; Fox, D. J.; Bergman, R. G. Acc. Chem. Res. 2002, 35, 44.
25. (b) Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163.
26. Lukehart, C. M. Fundamental Transition Metal Organometallic Chemistry; Wadsworth Inc.: California, 1985.
27. 2) complexes: (a) van den Broeke, J.; Heeringa, J. J. H.; Chuchuryukin, A. V.; Kooijman, H.; Mills, A. M.; Spek, A. L.; van Lenthe, J. H.; Ruttink, P. J. A.; Deelman, B. J.; van Koten, G. Organometallics 2004, 23, 2287. (b) Bera, P. S.; Sengupta, P. S.; De, G. S. Inorg. Reac. Mech. 2003, 5, 65. (c) Sun, X. J.; Jin, C.; Mei, Y. H.; Yang, G. S.; Quo, Z. J.; Zhu, L. G. Inorg. Chem. 2004, 43, 290. (d) Bera, P. S.; Chandra, S. K.; De, G. S. Int. J. Chem. Kinet. 2003, 53, 252. (e) Gerdes, G.; Chen, P. Organometallics 2003, 22, 2217. (f) Anandhi, U.; Holbert, T.; Lueng, D.; Sharp, P. R. Inorg. Chem. 2003, 42, 1282
28. 2) complexes: (a) van den Broeke, J.; Heeringa, J. J. H.; Chuchuryukin, A. V.; Kooijman, H.; Mills, A. M.; Spek, A. L.; van Lenthe, J. H.; Ruttink, P. J. A.; Deelman, B. J.; van Koten, G. Organometallics 2004, 23, 2287. (b) Bera, P. S.; Sengupta, P. S.; De, G. S. Inorg. Reac. Mech. 2003, 5, 65. (c) Sun, X. J.; Jin, C.; Mei, Y. H.; Yang, G. S.; Quo, Z. J.; Zhu, L. G. Inorg. Chem. 2004, 43, 290. (d) Bera, P. S.; Chandra, S. K.; De, G. S. Int. J. Chem. Kinet. 2003, 53, 252. (e) Gerdes, G.; Chen, P. Organometallics 2003, 22, 2217. (f) Anandhi, U.; Holbert, T.; Lueng, D.; Sharp, P. R. Inorg. Chem. 2003, 42, 1282
29. 2) complexes: (a) van den Broeke, J.; Heeringa, J. J. H.; Chuchuryukin, A. V.; Kooijman, H.; Mills, A. M.; Spek, A. L.; van Lenthe, J. H.; Ruttink, P. J. A.; Deelman, B. J.; van Koten, G. Organometallics 2004, 23, 2287. (b) Bera, P. S.; Sengupta, P. S.; De, G. S. Inorg. Reac. Mech. 2003, 5, 65. (c) Sun, X. J.; Jin, C.; Mei, Y. H.; Yang, G. S.; Quo, Z. J.; Zhu, L. G. Inorg. Chem. 2004, 43, 290. (d) Bera, P. S.; Chandra, S. K.; De, G. S. Int. J. Chem. Kinet. 2003, 53, 252. (e) Gerdes, G.; Chen, P. Organometallics 2003, 22, 2217. (f) Anandhi, U.; Holbert, T.; Lueng, D.; Sharp, P. R. Inorg. Chem. 2003, 42, 1282
30. 2) complexes: (a) van den Broeke, J.; Heeringa, J. J. H.; Chuchuryukin, A. V.; Kooijman, H.; Mills, A. M.; Spek, A. L.; van Lenthe, J. H.; Ruttink, P. J. A.; Deelman, B. J.; van Koten, G. Organometallics 2004, 23, 2287. (b) Bera, P. S.; Sengupta, P. S.; De, G. S. Inorg. Reac. Mech. 2003, 5, 65. (c) Sun, X. J.; Jin, C.; Mei, Y. H.; Yang, G. S.; Quo, Z. J.; Zhu, L. G. Inorg. Chem. 2004, 43, 290. (d) Bera, P. S.; Chandra, S. K.; De, G. S. Int. J. Chem. Kinet. 2003, 53, 252. (e) Gerdes, G.; Chen, P. Organometallics 2003, 22, 2217. (f) Anandhi, U.; Holbert, T.; Lueng, D.; Sharp, P. R. Inorg. Chem. 2003, 42, 1282
31. 2) complexes: (a) van den Broeke, J.; Heeringa, J. J. H.; Chuchuryukin, A. V.; Kooijman, H.; Mills, A. M.; Spek, A. L.; van Lenthe, J. H.; Ruttink, P. J. A.; Deelman, B. J.; van Koten, G. Organometallics 2004, 23, 2287. (b) Bera, P. S.; Sengupta, P. S.; De, G. S. Inorg. Reac. Mech. 2003, 5, 65. (c) Sun, X. J.; Jin, C.; Mei, Y. H.; Yang, G. S.; Quo, Z. J.; Zhu, L. G. Inorg. Chem. 2004, 43, 290. (d) Bera, P. S.; Chandra, S. K.; De, G. S. Int. J. Chem. Kinet. 2003, 53, 252. (e) Gerdes, G.; Chen, P. Organometallics 2003, 22, 2217. (f) Anandhi, U.; Holbert, T.; Lueng, D.; Sharp, P. R. Inorg. Chem. 2003, 42, 1282
32. 2) complexes: (a) van den Broeke, J.; Heeringa, J. J. H.; Chuchuryukin, A. V.; Kooijman, H.; Mills, A. M.; Spek, A. L.; van Lenthe, J. H.; Ruttink, P. J. A.; Deelman, B. J.; van Koten, G. Organometallics 2004, 23, 2287. (b) Bera, P. S.; Sengupta, P. S.; De, G. S. Inorg. Reac. Mech. 2003, 5, 65. (c) Sun, X. J.; Jin, C.; Mei, Y. H.; Yang, G. S.; Quo, Z. J.; Zhu, L. G. Inorg. Chem. 2004, 43, 290. (d) Bera, P. S.; Chandra, S. K.; De, G. S. Int. J. Chem. Kinet. 2003, 53, 252. (e) Gerdes, G.; Chen, P. Organometallics 2003, 22, 2217. (f) Anandhi, U.; Holbert, T.; Lueng, D.; Sharp, P. R. Inorg. Chem. 2003, 42, 1282
33. Structurally characterized terminal-hydroxo platinum complexes: (a) Flint, B.; Li, J. J.; Sharp, P. R. Organometallics 2002, 21, 997. (b) Straub, B. F.; Rominger, F.; Hoffman, P. Inorg. Chem. Comm. 2000, 3, 214. (c) Klein, A.; Klinkhammer, K.-W.; Scheiring, T. J. Organomet. Chem. 1999, 592, 128. (d) Navaro, J. A. R.; Romero, M. A.; Salas, J. M.; Quiros, M. Inorg. Chem. 1997, 36, 3277. (e) Miyamoto, T. K. Chem. Lett. 1994, 1971. (f) Britten, J. F.; Lippert, B.; Lock, C. J. L.; Pilon, P. Inorg. Chem. 1982, 21, 1936.
34. Structurally characterized terminal-hydroxo platinum complexes: (a) Flint, B.; Li, J. J.; Sharp, P. R. Organometallics 2002, 21, 997. (b) Straub, B. F.; Rominger, F.; Hoffman, P. Inorg. Chem. Comm. 2000, 3, 214. (c) Klein, A.; Klinkhammer, K.-W.; Scheiring, T. J. Organomet. Chem. 1999, 592, 128. (d) Navaro, J. A. R.; Romero, M. A.; Salas, J. M.; Quiros, M. Inorg. Chem. 1997, 36, 3277. (e) Miyamoto, T. K. Chem. Lett. 1994, 1971. (f) Britten, J. F.; Lippert, B.; Lock, C. J. L.; Pilon, P. Inorg. Chem. 1982, 21, 1936.
35. Structurally characterized terminal-hydroxo platinum complexes: (a) Flint, B.; Li, J. J.; Sharp, P. R. Organometallics 2002, 21, 997. (b) Straub, B. F.; Rominger, F.; Hoffman, P. Inorg. Chem. Comm. 2000, 3, 214. (c) Klein, A.; Klinkhammer, K.-W.; Scheiring, T. J. Organomet. Chem. 1999, 592, 128. (d) Navaro, J. A. R.; Romero, M. A.; Salas, J. M.; Quiros, M. Inorg. Chem. 1997, 36, 3277. (e) Miyamoto, T. K. Chem. Lett. 1994, 1971. (f) Britten, J. F.; Lippert, B.; Lock, C. J. L.; Pilon, P. Inorg. Chem. 1982, 21, 1936.
36. Structurally characterized terminal-hydroxo platinum complexes: (a) Flint, B.; Li, J. J.; Sharp, P. R. Organometallics 2002, 21, 997. (b) Straub, B. F.; Rominger, F.; Hoffman, P. Inorg. Chem. Comm. 2000, 3, 214. (c) Klein, A.; Klinkhammer, K.-W.; Scheiring, T. J. Organomet. Chem. 1999, 592, 128. (d) Navaro, J. A. R.; Romero, M. A.; Salas, J. M.; Quiros, M. Inorg. Chem. 1997, 36, 3277. (e) Miyamoto, T. K. Chem. Lett. 1994, 1971. (f) Britten, J. F.; Lippert, B.; Lock, C. J. L.; Pilon, P. Inorg. Chem. 1982, 21, 1936.
37. Structurally characterized terminal-hydroxo platinum complexes: (a) Flint, B.; Li, J. J.; Sharp, P. R. Organometallics 2002, 21, 997. (b) Straub, B. F.; Rominger, F.; Hoffman, P. Inorg. Chem. Comm. 2000, 3, 214. (c) Klein, A.; Klinkhammer, K.-W.; Scheiring, T. J. Organomet. Chem. 1999, 592, 128. (d) Navaro, J. A. R.; Romero, M. A.; Salas, J. M.; Quiros, M. Inorg. Chem. 1997, 36, 3277. (e) Miyamoto, T. K. Chem. Lett. 1994, 1971. (f) Britten, J. F.; Lippert, B.; Lock, C. J. L.; Pilon, P. Inorg. Chem. 1982, 21, 1936.
38. Structurally characterized terminal-hydroxo platinum complexes: (a) Flint, B.; Li, J. J.; Sharp, P. R. Organometallics 2002, 21, 997. (b) Straub, B. F.; Rominger, F.; Hoffman, P. Inorg. Chem. Comm. 2000, 3, 214. (c) Klein, A.; Klinkhammer, K.-W.; Scheiring, T. J. Organomet. Chem. 1999, 592, 128. (d) Navaro, J. A. R.; Romero, M. A.; Salas, J. M.; Quiros, M. Inorg. Chem. 1997, 36, 3277. (e) Miyamoto, T. K. Chem. Lett. 1994, 1971. (f) Britten, J. F.; Lippert, B.; Lock, C. J. L.; Pilon, P. Inorg. Chem. 1982, 21, 1936.
39. Clark, H. C.; Goel, A. B.; Wong, C. S. Inorg. Chim. Acta 1979, 159, 34.
40. Clark. H. C.; Manzer, L. E. J. Organomet. Chem. 1973, 59, 411.