A phosphane-free catalyst system for the heck arylation of disubstituted alkenes: Application to the synthesis of trisubstituted olefins

Chemistry - A European Journal

Volumn 5, Issue 11, 1999, Pages 3107-3112

  Gürtler, Christoph ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Alkenes; Base effects; Heck reaction; Palladium; Phase transfer catalysis

Indexed keywords

ALKENE DERIVATIVE; DICYCLOHEXYLAMINE DERIVATIVE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; ELECTRON; PHASE TRANSITION; STEREOCHEMISTRY; SYNTHESIS; THERMODYNAMICS;

EID: 0032731198     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19991105)5:11<3107::AID-CHEM3107>3.0.CO;2-#     Document Type: Article

References (45)

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3. For a recent review see: A. de Meijere, F. E. Meyer Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379; W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2.
4. For a recent review see: A. de Meijere, F. E. Meyer Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379; W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2.
5. For a recent review see: A. de Meijere, F. E. Meyer Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379; W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2.
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8. c) A. Amorese, A. Arcadi, E. Bernocchi, S. Cacchi, S. Cerrine, W. Fedeli, G. Ortar, Tetrahedron 1989, 45, 813. This system gives good results but seems to be limited to benzylideneacetone as an olefin;
9. d) S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar Tetrahedron Lett. 1987, 28, 3039. This system was applied to the vinylation of methyl α-methoxyacrylate to give α-keto acid derivatives in moderate yields starting from aryl iodides;
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11. f) Some studies of the synthesis of arylated didehydroamino acid derivatives are available, see, for example, A.-S. Carlström, T. Frejd, Synthesis 1989, 414;
12. g) After the submission of this manuscript a report appeared on a study of the Heck reaction of acrylates supported on a soluble polymeric support: C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, Tetrahedron Lett. 1999, 40, 2101.
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15. See for example R. F. Heck, Pure Appl. Chem. 1978, 50, 691.
16. Surprisingly, there are only a few examples of the influence of different bases on the reaction rate and the E/Z selectivity in Heck reactions. See ref. [3b] and a) M. Beller, T. H. Riermeier, Tetrahedron Lett. 1996, 37, 6535. This catalyst system proved to be very effective for the Heck vinylation of aryl halides with n-butyl acrylate giving very high turnover numbers, but requires high reaction temperatures (140 C); b) R. C. Larock, S. Babu, Tetrahedron Lett. 1987, 28, 5291.
17. Surprisingly, there are only a few examples of the influence of different bases on the reaction rate and the E/Z selectivity in Heck reactions. See ref. [3b] and a) M. Beller, T. H. Riermeier, Tetrahedron Lett. 1996, 37, 6535. This catalyst system proved to be very effective for the Heck vinylation of aryl halides with n-butyl acrylate giving very high turnover numbers, but requires high reaction temperatures (140 C); b) R. C. Larock, S. Babu, Tetrahedron Lett. 1987, 28, 5291.
18. a) For a recent review see T. Jeffery in Advances in Metal-Organic Chemistry. Vol. 5 (Ed.: L. S. Liebeskind), JAI Press Inc., 1996, 153.;
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24. Tetraethylammonium chloride (98%) was purchased from Fluka Chemicals. Anhydrous reaction conditions were used.
25. A system developed by Herrmann and Beller proved to be very efficient for the Heck and Suzuki type reactions with very high turnover numbers, but required relatively high temperatures (140°C). See ref. [6] and W. A. Herrmann, C. Broßmer, K. Öfele, M. Beller, H. Fischer, J. Mol. Catal., 1995, 103, 133; W. A. Herrmann, C. Brossmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. Int. Ed. Engl. 1995, 34, 1844; Angew. Chem. 1995, 107, 1989; W. A. Herrmann, C. Brossmer, C.-P. Reisinger, T. H. Riermeier, K. Öfele, M. Beller, Chem. Eur. J. 1997, 3, 1357.
26. A system developed by Herrmann and Beller proved to be very efficient for the Heck and Suzuki type reactions with very high turnover numbers, but required relatively high temperatures (140°C). See ref. [6] and W. A. Herrmann, C. Broßmer, K. Öfele, M. Beller, H. Fischer, J. Mol. Catal., 1995, 103, 133; W. A. Herrmann, C. Brossmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. Int. Ed. Engl. 1995, 34, 1844; Angew. Chem. 1995, 107, 1989; W. A. Herrmann, C. Brossmer, C.-P. Reisinger, T. H. Riermeier, K. Öfele, M. Beller, Chem. Eur. J. 1997, 3, 1357.
27. A system developed by Herrmann and Beller proved to be very efficient for the Heck and Suzuki type reactions with very high turnover numbers, but required relatively high temperatures (140°C). See ref. [6] and W. A. Herrmann, C. Broßmer, K. Öfele, M. Beller, H. Fischer, J. Mol. Catal., 1995, 103, 133; W. A. Herrmann, C. Brossmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. Int. Ed. Engl. 1995, 34, 1844; Angew. Chem. 1995, 107, 1989; W. A. Herrmann, C. Brossmer, C.-P. Reisinger, T. H. Riermeier, K. Öfele, M. Beller, Chem. Eur. J. 1997, 3, 1357.
28. A system developed by Herrmann and Beller proved to be very efficient for the Heck and Suzuki type reactions with very high turnover numbers, but required relatively high temperatures (140°C). See ref. [6] and W. A. Herrmann, C. Broßmer, K. Öfele, M. Beller, H. Fischer, J. Mol. Catal., 1995, 103, 133; W. A. Herrmann, C. Brossmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. Int. Ed. Engl. 1995, 34, 1844; Angew. Chem. 1995, 107, 1989; W. A. Herrmann, C. Brossmer, C.-P. Reisinger, T. H. Riermeier, K. Öfele, M. Beller, Chem. Eur. J. 1997, 3, 1357.
29. See, for example: A. Spencer, J. Organomet. Chem. 1983, 258, 102.
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33. N. A. Cortese, C. B. Ziegler, Jr., B. Hrnjez, R. F. Heck, J. Org. Chem. 1978, 43, 2952.
34. [4b] this was found to give considerably slower reactions and lower yields.
35. Because of the enamide nature of this product, isomerization takes place. This was checked by the isomerization of the pure E isomer under the reaction conditions.
36. a) J. B. Melpolder, R. F. Heck, J. Org. Chem. 1976, 41, 265;
37. b) R. F. Heck, Org. React. 1982, 27, 345. and references therein;
38. c) S. Kagabo, Y. Shimizu, I. Chinatsu, K. Moriya, Synthesis 1992, 9, 830; R. Sarges, J. R. Tretter, J. Org. Chem. 1974, 39, 1710.
39. c) S. Kagabo, Y. Shimizu, I. Chinatsu, K. Moriya, Synthesis 1992, 9, 830; R. Sarges, J. R. Tretter, J. Org. Chem. 1974, 39, 1710.
40. The coupling of 2-ethyliodobenzene and 4-ethyliodobenzene led to the formation of the (o-ethylphenyl)-3-methylmethyl acrylate in low yields (30% and 40% and a E/Z ratio of 4:1 and 2:1 respectively).
41. K. Kudo, M. Hidai, T. Murayama, Y. Uchida, Chemical Communication 1970, 1701.
42. A. Hallberg, K. Karabelas, J. Org. Chem. 1986, 51, 5286.
43. The structure of the product of the double Heck reaction is as follows: (Equation Presented)
44. [3a]
45. F. Camps, J. Coll, M. E. Seba, An. Quim. Ser. C 1980, 76, 61.