Cationic Intermediates in the Intramolecular Insertion of Alkenes into (η3-Allyl)palladium(II) Complexes

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 7, 1997, Pages 767-769

  Gómez Bengoa, Enrique ^a   Cuerva, Juan Manuel ^a   Echavarren, Antonio M ^a   Martorell, Gabriel ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITAT DE LES ILLES BALEARS   (Spain)

Author keywords

Allyl complexes; Carbocycles; Cyclizations; Insertions; Palladium

Indexed keywords

EID: 0030838879     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199707671     Document Type: Article

References (42)

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2. Reviews: a) W. Oppolzer in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, chapter 8.3; b) W. Oppolzer in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, chapter 1.2.
3. Recent reviews: a) W. Oppolzer, J. Ruiz-Montes, Helv. Chim. Acta 1993, 76, 1266; b) N.C.Ihle, C.H. Heathcock, J. Org. Chem, 1993,58,560; K. Hiroi, K. Hirasawa, Chem. Pharm. Bull. 1994, 42, 786; T. Doi, A. Yanagisawa, S. Nakanishi, K. Yamamoto, T. Takahashi, J. Org. Chem. 1996, 61, 2602.
4. Recent reviews: a) W. Oppolzer, J. Ruiz-Montes, Helv. Chim. Acta 1993, 76, 1266; b) N.C.Ihle, C.H. Heathcock, J. Org. Chem, 1993,58,560; K. Hiroi, K. Hirasawa, Chem. Pharm. Bull. 1994, 42, 786; T. Doi, A. Yanagisawa, S. Nakanishi, K. Yamamoto, T. Takahashi, J. Org. Chem. 1996, 61, 2602.
5. Recent reviews: a) W. Oppolzer, J. Ruiz-Montes, Helv. Chim. Acta 1993, 76, 1266; b) N.C.Ihle, C.H. Heathcock, J. Org. Chem, 1993,58,560; K. Hiroi, K. Hirasawa, Chem. Pharm. Bull. 1994, 42, 786; T. Doi, A. Yanagisawa, S. Nakanishi, K. Yamamoto, T. Takahashi, J. Org. Chem. 1996, 61, 2602.
6. Recent reviews: a) W. Oppolzer, J. Ruiz-Montes, Helv. Chim. Acta 1993, 76, 1266; b) N.C.Ihle, C.H. Heathcock, J. Org. Chem, 1993,58,560; K. Hiroi, K. Hirasawa, Chem. Pharm. Bull. 1994, 42, 786; T. Doi, A. Yanagisawa, S. Nakanishi, K. Yamamoto, T. Takahashi, J. Org. Chem. 1996, 61, 2602.
7. Cyclization only takes place in common solvents for substrates with a 4-hydroxyl group, which apparently coordinates to the metal: E. Negishi, S. lyer, C. J. Rousset, Tetrahedron Lett. I. 1989, 30, 291.
8. 3-allylpalIadium(II) complexes: S. A. Godleski in Comprehensive Organic Synthesis, Vol. 4 (Eds. : B. M. Trost, l. Fleming). Pergamon, Oxford, 1991, pp. 601-602, 625.
9. Cyclization of an allyl alcohol to yield a six-membered ring: E. Gômez-Bengoa, P. Noheda, A. M. Echavarren, Tetrahedron Lett. 1994, 35, 7097.
10. A. Vitagliano, B. Åkermark, S. Hansson, Organometullics 1991, 10, 2592.
11. 3-allyl)palladium(II) complexes from palladium(0) phosphane complexes: T. Yamamoto, Q. Suito, A. Yamamoto, J. Am. Chem. Soc. 1981, 103, 5600.
12. T. Ukai, H. Kawazura, Y. Ishii, J. J. Bonnett, J. A. Ibers, J. Organomet. Chem. 1974, 65, 253.
13. a) B. Åkermark, A. Vitagliano, Organometallics 1985, 4, 1275:
14. b) R. Ciajolo. M. A. Jama, A. Tuzi, A. Vitagliano, J. Organomet. Chem. 1985, 295, 233.
15. R. P. Hughes, T. Jack, J. Powell, J. Organomet. Chem. 1973, 63, 451.
16. 3-allyl) and H-7 (alkenyl).
17. W. Oppolzer, J.-M. Gaudin, Helv. Chim. Acta 1987, 70, 1477.
18. J.-E. Bäckvall, R. E. Nordberg, D. Wilhelm, J. Am. Chem. Soc. 1985, 107, 6892. and references therein.
19. M. P. T. Sjögren, S. Hansson, B. Åkermark, A. Vitagliano, Organometallics 1994, 13, 1963. and references therein.
20. 3-allyl ligand, a consequence of a rapid ligand-exchange process. See also a) A. Gogoll, J. Örnebro, H. Grennberg, J.-E. Bäckvall, J. Am. Chem. Soc. 1994, 116, 3631; b) C. Breutel, P.S. Pregosin, R. Salzmann, A. Togni, ibid. 1994, 116, 4067.
21. 3-allyl ligand, a consequence of a rapid ligand-exchange process. See also a) A. Gogoll, J. Örnebro, H. Grennberg, J.-E. Bäckvall, J. Am. Chem. Soc. 1994, 116, 3631; b) C. Breutel, P.S. Pregosin, R. Salzmann, A. Togni, ibid. 1994, 116, 4067.
22. -3M in toluene, 90° C, 16 h) led to the formation of a mixture of 11 and 12 in moderate yield. We thank one of the referees for suggesting this experiment.
23. C. A. Tolman, Chem. Rev. 1977, 77, 313.
24. 3 as the ligand provided 11 in 52% yield in DME under reflux.
25. 2. 40° C) led to 11 in similar yield.
26. The NMR data or 13 are consistent with the cyclic structure shown (Table 1). In contrast, a lower homologue of 13 prefers an open halogen-bridged dimeric structure: R. P. Hughes, T. Jack, J. Powell, J. Organomet. Chem. 1973, 63, 451.
27. The high affinity of water for palladium in cationic complexes has been demonstrated: a) J. M. Brown, K. K. Hii, Angew. Chem. 1996, 108, 679; Angew. Chem. Int. Ed. Engl. 1996, 35, 657; b) P. J. Stang, D. H. Cao, G. T. Poulter, A. M. Arif, Organometallics 1995, 14, 1110; G. M. DiRenzo, P. S. White, M. Brookhart, J. Am. Chem. Soc. 1996, 118, 6225.
28. The high affinity of water for palladium in cationic complexes has been demonstrated: a) J. M. Brown, K. K. Hii, Angew. Chem. 1996, 108, 679; Angew. Chem. Int. Ed. Engl. 1996, 35, 657; b) P. J. Stang, D. H. Cao, G. T. Poulter, A. M. Arif, Organometallics 1995, 14, 1110; G. M. DiRenzo, P. S. White, M. Brookhart, J. Am. Chem. Soc. 1996, 118, 6225.
29. The high affinity of water for palladium in cationic complexes has been demonstrated: a) J. M. Brown, K. K. Hii, Angew. Chem. 1996, 108, 679; Angew. Chem. Int. Ed. Engl. 1996, 35, 657; b) P. J. Stang, D. H. Cao, G. T. Poulter, A. M. Arif, Organometallics 1995, 14, 1110; G. M. DiRenzo, P. S. White, M. Brookhart, J. Am. Chem. Soc. 1996, 118, 6225.
30. The high affinity of water for palladium in cationic complexes has been demonstrated: a) J. M. Brown, K. K. Hii, Angew. Chem. 1996, 108, 679; Angew. Chem. Int. Ed. Engl. 1996, 35, 657; b) P. J. Stang, D. H. Cao, G. T. Poulter, A. M. Arif, Organometallics 1995, 14, 1110; G. M. DiRenzo, P. S. White, M. Brookhart, J. Am. Chem. Soc. 1996, 118, 6225.
31. 2)]
32. b) W. Bauer, P. von R. Schleyer, Magn. Reson. Chem. 1988, 26, 827
33. 31P NMR spectrum of 10 between 0 and -80° C.
34. Three other olefin isomers were also obtained in addition to 11 and 12 (overall yield 65%).
35. 3 did not improved the yield. The best result was obtained in DME under reflux (9:1 mixture of 11 and 12, 81% yield).
36. 3]-dba and 1,4-bis(diphenylphosphane)butane or 1,1'bis(diphenylphosphane)ferrocene. 1,1-bis(diphenylphosphane)methane, which probably acts as a monodentate ligand, led to a 1.2:1 mixture of 11 and 12 (44% yield).
37. 1-allyl)palladium(II) complexes react with alkenes to yield [3 + 2] cycloadducts instead of insertion derivatives: H. Kurosawa, A. Urabe, K. Miki, N. Kasai, Organometallics 1986, 5, 2002. and references therein.
38. 1-allyl)palladium intermediates: a) R. P. Hughes, J. Powell, J. Organomet. Chem. 1973, 60, 387; b) ibid. 1973, 60, 409.
39. 1-allyl)palladium intermediates: a) R. P. Hughes, J. Powell, J. Organomet. Chem. 1973, 60, 387; b) ibid. 1973, 60, 409.
40. a) S. Mecking, W. Keim, Organometallics 1996, 15, 2650
41. b) see ref. [21c].
42. J. Tsuji, Palladium Reagents and Catalysis, Wiley, Chichester, 1995.