Cationic palladium η3-allyl complexes with hemilabile P,O-ligands: Synthesis and reactivity. Insertion of ethylene into the Pd-allyl function

Organometallics

Volumn 15, Issue 11, 1996, Pages 2650-2656

  Mecking, Stefan ^a   Keim, Wilhelm ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001618381     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960061z     Document Type: Article

References (55)

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26. Very recently, the reaction of similar palladium allyl complexes with various olefins was directly observed by NMR spectroscopy: DiRenzo, G. M.; Brookhart, M. J. Am. Chem. Soc., in press.
27. For similar complexes, prepared by different routes see: (a) Lehmkuhl, H.; Rufinska, A.; Benn, R.; Schroth, G.; Mynott, R. Liebigs Ann. Chem. 1981, 317-332. (b) Parra-Hake, M.; Rettig, M. F.; Williams, J. L.; Wing, R. M. Organometallics 1986 5, 1032-1040. (c) Flood, T. C.; Statler, J. A. Organometallics 1984, 3, 1795-1803. (d) Flood, T. C.; Bittler, S. P. J. Am. Chem. Soc. 1984, 106, 6076-6077. (e) Ermer, S. P.; Struck, G. E.; Bitler, S. P.; Richards, R.; Bau, R.; Flood, T. C. Organometallics 1993, 12, 2634-2643. (f) Pedone, C.; Benedetti, E. J. Organomet. Chem. 1971, 31, 403-414.
28. For similar complexes, prepared by different routes see: (a) Lehmkuhl, H.; Rufinska, A.; Benn, R.; Schroth, G.; Mynott, R. Liebigs Ann. Chem. 1981, 317-332. (b) Parra-Hake, M.; Rettig, M. F.; Williams, J. L.; Wing, R. M. Organometallics 1986 5, 1032-1040. (c) Flood, T. C.; Statler, J. A. Organometallics 1984, 3, 1795-1803. (d) Flood, T. C.; Bittler, S. P. J. Am. Chem. Soc. 1984, 106, 6076-6077. (e) Ermer, S. P.; Struck, G. E.; Bitler, S. P.; Richards, R.; Bau, R.; Flood, T. C. Organometallics 1993, 12, 2634-2643. (f) Pedone, C.; Benedetti, E. J. Organomet. Chem. 1971, 31, 403-414.
29. For similar complexes, prepared by different routes see: (a) Lehmkuhl, H.; Rufinska, A.; Benn, R.; Schroth, G.; Mynott, R. Liebigs Ann. Chem. 1981, 317-332. (b) Parra-Hake, M.; Rettig, M. F.; Williams, J. L.; Wing, R. M. Organometallics 1986 5, 1032-1040. (c) Flood, T. C.; Statler, J. A. Organometallics 1984, 3, 1795-1803. (d) Flood, T. C.; Bittler, S. P. J. Am. Chem. Soc. 1984, 106, 6076-6077. (e) Ermer, S. P.; Struck, G. E.; Bitler, S. P.; Richards, R.; Bau, R.; Flood, T. C. Organometallics 1993, 12, 2634-2643. (f) Pedone, C.; Benedetti, E. J. Organomet. Chem. 1971, 31, 403-414.
30. For similar complexes, prepared by different routes see: (a) Lehmkuhl, H.; Rufinska, A.; Benn, R.; Schroth, G.; Mynott, R. Liebigs Ann. Chem. 1981, 317-332. (b) Parra-Hake, M.; Rettig, M. F.; Williams, J. L.; Wing, R. M. Organometallics 1986 5, 1032-1040. (c) Flood, T. C.; Statler, J. A. Organometallics 1984, 3, 1795-1803. (d) Flood, T. C.; Bittler, S. P. J. Am. Chem. Soc. 1984, 106, 6076-6077. (e) Ermer, S. P.; Struck, G. E.; Bitler, S. P.; Richards, R.; Bau, R.; Flood, T. C. Organometallics 1993, 12, 2634-2643. (f) Pedone, C.; Benedetti, E. J. Organomet. Chem. 1971, 31, 403-414.
31. For similar complexes, prepared by different routes see: (a) Lehmkuhl, H.; Rufinska, A.; Benn, R.; Schroth, G.; Mynott, R. Liebigs Ann. Chem. 1981, 317-332. (b) Parra-Hake, M.; Rettig, M. F.; Williams, J. L.; Wing, R. M. Organometallics 1986 5, 1032-1040. (c) Flood, T. C.; Statler, J. A. Organometallics 1984, 3, 1795-1803. (d) Flood, T. C.; Bittler, S. P. J. Am. Chem. Soc. 1984, 106, 6076-6077. (e) Ermer, S. P.; Struck, G. E.; Bitler, S. P.; Richards, R.; Bau, R.; Flood, T. C. Organometallics 1993, 12, 2634-2643. (f) Pedone, C.; Benedetti, E. J. Organomet. Chem. 1971, 31, 403-414.
32. For similar complexes, prepared by different routes see: (a) Lehmkuhl, H.; Rufinska, A.; Benn, R.; Schroth, G.; Mynott, R. Liebigs Ann. Chem. 1981, 317-332. (b) Parra-Hake, M.; Rettig, M. F.; Williams, J. L.; Wing, R. M. Organometallics 1986 5, 1032-1040. (c) Flood, T. C.; Statler, J. A. Organometallics 1984, 3, 1795-1803. (d) Flood, T. C.; Bittler, S. P. J. Am. Chem. Soc. 1984, 106, 6076-6077. (e) Ermer, S. P.; Struck, G. E.; Bitler, S. P.; Richards, R.; Bau, R.; Flood, T. C. Organometallics 1993, 12, 2634-2643. (f) Pedone, C.; Benedetti, E. J. Organomet. Chem. 1971, 31, 403-414.
33. This observation must be kept in mind, when estimating the coordination behavior of the P,O-ligand in an assumed intermediate in catalysis from the relative coordination strength of the oxygen donor in model compounds, such as 2-4, as the other ligands coordinated to the metal center obviously have a strong impact.
34. c ≈ 17°C (300 MHz). It is assumed that this exchange occurs between two species with opposite enantiotopic faces of the olefinic moiety binding to the metal center. This requires intermediate decoordination of the olefinic function.
35. 13C NMR data cf. ref 15e. The J(H,P) values provide no clear picture considering the stereochemistry in comparison to literature data: (a) de Graaf, W.; Boersma, J.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. Organometallics 1989, 8, 2907-2917. (b) Lindner, E.; Dettinger, J.; Fawzi, R.; Steimann, M. Chem. Ber. 1993, 126, 1347-1353.
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37. Mecking, S. Dissertation, RWTH Aachen, 1994.
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55. 31P NMR data for all ligands, cf. ref 19.