Palladium-catalyzed cross-coupling reaction of allyl carbonates with organostannanes

Tetrahedron Letters

Volumn 37, Issue 36, 1996, Pages 6587-6590

  Castaño, Ana M ^a   Echavarren, Antonio M ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CYCLOPENTANE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030565554     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01406-2     Document Type: Article

References (32)

1. (a) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995; Chapter 4.
2. (b) Farina, F. In Comprehensive Organometallic Chemistry II; Abel, E.W.; Stone, F.G.A.; Wilkinson, G. Eds., Pergamon: Oxford, 1995; Vol. 12, Chapter 3.4.
3. (a) Stille, J.K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
4. (b) Mitchell, T.N. Synthesis 1992, 803.
5. Ritter, K. Synthesis 1993, 735.
6. For a recent review, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
7. For applications of allyl-palladium chemistry in organic synthesis, see: (a) Godleski, S.A. in Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chaper 3.3.
8. (b) Harrington, P.J. In Comprehensive Organometallic Chemistry; Abel, E.W.; Stone, F.G.A.; Wilkinson, G. Eds., Pergamon: Oxford, 1995; Vol. 12, Chapter 8.2.
9. Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester; 1995, Chapter 4.2.
10. (a) Sheffy, F.K.; Stille, J.K. J. Am. Chem. Soc. 1983, 105, 7173.
11. (b) Sheffy, F.K.; Godschalx, J.P.; Stille, J.K. J. Am. Chem. Soc. 1984, 106, 4833, and references therein.
12. Del Valle, L; Stille, J.K.; Hegedus, L.S. J. Org. Chem. 1990, 55, 3019.
13. For the use of other leaving groups, see: Malet, R.; Moreno-Mañas, M.; Pleixats, R. An. Quim. Int. Ed. 1996, 92, 25, and references therein.
14. 2": (a) Takahashi, Y.; Ito, T.; Sakai, S.; Ishii, Y. J. Chem. Soc., Chem. Commun. 1970, 1065.
15. (b) Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J.J.; Ibers, J.A. J. Organomet. Chem. 1974, 65, 253.
16. The Stille reaction with vinyl epoxides proceeds under similar conditions: (a) Tueting, D.R.; Echavarren, A.M.; Stille, J.K. Tetrahedron 1989, 45, 979.
17. (b) Tueting, D.R.; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1988, 110, 4039.
18. Castano, A.M.; Ruano, M.; Echavarren, A.M. Tetrahedron Lett, following communication.
19. For the palladium-catalyzed reaction of allyl carbonates with malonate type nucleophiles, see: (a) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y. Tetrahedron Lett. 1982, 23, 4809.
20. (b) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y.; Sugiura, T. J. Org. Chem. 1985, 50, 1523. For reviews, see:
21. Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140.
22. Tsuji, J. Tetrahedron 1986, 42, 4361.
23. 9
24. (b) For an example of the beneficial effect of water in palladium-catalyzed reactions, see: Zhang, H.-C.; Daves, G.D. Organometallics 1993, 12, 1499.
25. Ghosal, S.; Luke, G. P.; Kyler, K. S. J. Org. Chem. 1987, 52, 4296.
26. 3-allyl)palladium complexes from allyl trifluoroacetates, see: Vitagliano, A.; Åkermark, B.; Hansson, S. Organometallics 1991,10, 2592.
27. 5 However, we have observed substantial isomerization in the coupling of geranyl chloride under the described conditions.
28. 15
29. (b) See also: Åkermark, B.; Vitagliano, A. Organometallics 1985, 4, 1275.
30. 3-allyl)palladium intermediates in this solvent For the Pd(0)-catalyzed alkylation reaction of allyl electrophiles with stabilized nucleophiles in water, see: Blart, E.; Genet, G.P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron. 1994, 50, 505.
31. 2O were obtained as the tin byproducts.
32. 3-allyl)palladium carbonates in the presence of water, see: Ozawa, F.; Son, T.; Ebina, S.; Osakada, K.; Yamamoto, A. Organometallics 1992, 11, 171.