Vinylic deprotonation in the coordination sphere of platinum(II): Regioselective formation of alkenyl complexes

European Journal of Inorganic Chemistry

Volumn , Issue 24, 2004, Pages 4751-4754

  Lorusso, Giuseppe ^a   Boccaletti, Giovanni ^a   Di Masi, Nicola G ^a   Fanizzi, Francesco P ^b,c   Maresca, Luciana ^a   Natile, Giovanni ^a  

^a UNIVERSITY OF BARI   (Italy)

^b UNIVERSITY OF SALENTO   (Italy)

^c Cancer Research Center ^*  (Italy)

Author keywords

(E) (Z) isomerization; Alkenes; Br nsted acidity; Deprotonation reaction; Platinum

Indexed keywords

COORDINATION REACTIONS; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLATINUM COMPOUNDS;

(E)/(Z) ISOMERIZATION; ALKENYL; ALKENYL COMPLEXES; BRÖNSTED ACIDITY; COORDINATION SPHERE; DEPROTONATION REACTION; ISOMERISATION; PLATINUM SPECIES; REGIO-SELECTIVE; TETRAMETHYLETHYLENEDIAMINE;

ISOMERS;

ALKENE; ALKENYL GROUP; PLATINUM DERIVATIVE; SOLVENT; VINYL DERIVATIVE;

ACIDITY; ARTICLE; BRONSTED ACIDITY; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHLORINATION; COMPLEX FORMATION; DEPROTONATION; ELECTRON TRANSPORT; ISOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT;

EID: 11244292845     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200400512     Document Type: Article

References (25)

1. [1a] G. Bandoli, A. Dolmella, F. P. Fanizzi, N. G. Di Masi, L. Maresca, G. Natile, Organometallics 2001, 20, 805-807.
2. [1b] G. Bandoli, A. Dolmella, F. P. Fanizzi, N. G. Di Masi, L. Maresca, G. Natile, Organometallics 2002, 21, 4595.
3. [2a] W. P. Giering, S. Raghu, M. Rosenblum, A. Cutler, D. Ehntholt, R. W. Fish, J. Am. Chem. Soc. 1972, 94, 8251.
4. [2b] A. Cutler, D. Ehntholt, P. Lennon, K. Nicholas, D. F. Marten, M. Madhavarao, S. Raghu, A. Rosan, M. Rosenblum, J. Am. Chem. Soc. 1975, 97, 3149.
5. [2c] A. Cutler, D. Ehntholt, W. P. Giering, P. Lennon, S. Raghu, A. Rosan, M. Rosenblum, J. Tancrede, D. Wells, J. Am. Chem. Soc. 1976, 98, 3495.
6. [2d] P. Lennon, M. Rosenblum, J. Am. Chem. Soc. 1983, 105, 1233.
7. [3a] G. S. Bodner, K. Emerson, R. D. Larsen, J. A. Gladysz, Organometallics 1989, 8, 2399.
8. [3b] T. S. Peng, J. A. Gladysz, Organometallics 1990, 9, 2884.
9. [3c] J. J. Kowalczyk, A. M. Arif, J. A. Gladysz, Chem. Ber. 1991, 124, 729.
10. [3d] T. S. Peng, J. A. Gladysz, Organometallics 1995, 14, 898.
11. L. Giannini, G. Guillemot, E. Solari, C. Floriani, N. Re, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1999, 121, 2797.
12. [5a] S. A. Benyunes, M. Green, M. McPartlin, C. B. M. Nation, J. Chem. Soc., Chem. Commun. 1989, 1887.
13. [5b] S. A. Benyunes, R. J. Deeth, A. Fries, M. Green, M. McPartlin, C. B. M. Nation, J. Chem. Soc., Dalton Trans. 1992, 3453.
14. A. M. Gull, P. E. Fanwick, C. P. Kubiak, Organometallics 1993, 12, 2121.
15. C. Hahn, P. Morvillo, E. Herdtweck, A. Vitagliano, Organometallics 2002, 21, 1807.
16. Pt,H = 50 and 48 Hz for the more and the less shielded proton, respectively.
17. In the (Z) isomer the vinyl hydrogen signals appear at δ = 6.79 and 7.35 ppm, and the vinyl carbon signals at δ = 126.8 and 134.0 ppm; also in this case the more shielded carbon atom is bound to the less shielded proton.
18. 1H NMR spectrum: W. Yao, O. Eisenstein, R. H. Crabtree, Inorg. Chim. Acta 1997, 254, 105; L. Bremmer, J. M. Charnock, P. L. Goggin, R. J. Goodfellow, A. G. Orpen, T. F. Koetzle, J. Chem. Soc., Dalton Trans. 1991, 1789.
19. 1H NMR spectrum: W. Yao, O. Eisenstein, R. H. Crabtree, Inorg. Chim. Acta 1997, 254, 105; L. Bremmer, J. M. Charnock, P. L. Goggin, R. J. Goodfellow, A. G. Orpen, T. F. Koetzle, J. Chem. Soc., Dalton Trans. 1991, 1789.
20. 1H NMR spectrum: W. Yao, O. Eisenstein, R. H. Crabtree, Inorg. Chim. Acta 1997, 254, 105; L. Bremmer, J. M. Charnock, P. L. Goggin, R. J. Goodfellow, A. G. Orpen, T. F. Koetzle, J. Chem. Soc., Dalton Trans. 1991, 1789.
21. 1H NMR spectrum: W. Yao, O. Eisenstein, R. H. Crabtree, Inorg. Chim. Acta 1997, 254, 105; L. Bremmer, J. M. Charnock, P. L. Goggin, R. J. Goodfellow, A. G. Orpen, T. F. Koetzle, J. Chem. Soc., Dalton Trans. 1991, 1789.
22. F. P. Fanizzi, L. Maresca, G. Natile, C. Pacifico, Gazz. Chim. Ital. 1994, 124, 184.
23. L. Maresca, G. Natile, Comments Inorg. Chem. 1994, 16, 95.
24. [13a] When the vinylic C-H bond is closely parallel to the π electrons of the benzene ring, it is activated by σ-π* orbital interaction; similarly, the vinyl anion, generated by proton abstraction, is stabilized by delocalization to the phenyl ring. [13] H. Mori, T. Matsuo, Y. Yoshioka, S. Katsumura, Tetrahedron Lett. 2001, 42, 3093.
25. M. Meot-Ner, S. A. Kafafi, J. Am. Chem. Soc. 1988, 110, 6297.