First palladium-catalyzed Heck reactions with efficient colloidal catalyst systems

Journal of Organometallic Chemistry

Volumn 520, Issue 1-2, 1996, Pages 257-259

  Beller, Matthias ^a,b   Fischer, Hartmut ^a   Kühlein, Klaus ^a   Reisinger, C P ^b   Herrmann, W A ^b  

^a SANOFI   (France)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Catalysis; Colloids; Heck reaction; Palladium

Indexed keywords

EID: 0030576421     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0022-328X(96)06398-X     Document Type: Article

References (43)

1. [1] A. Tafesh and M. Beller, Tetrahedron Lett., 36 (1995) 9305.
2. [2] J. Tsuji, Palladium Reagents and Catalysts - Innovations in Organic Synthesis, Wiley, Chichester, UK, 1995; R.F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; M. Beller, B. Cornils, C.D. Frohning and C.W. Kohlpaintner, J. Mol. Catal., 104 (1995) 17; J. Tsuji, in B.M. Trost and I. Fleming (eds.), Comprehensive Organic Synthesis, Vol. 7, Pergamon Press, Oxford, 1991, p. 449.
3. [2] J. Tsuji, Palladium Reagents and Catalysts - Innovations in Organic Synthesis, Wiley, Chichester, UK, 1995; R.F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; M. Beller, B. Cornils, C.D. Frohning and C.W. Kohlpaintner, J. Mol. Catal., 104 (1995) 17; J. Tsuji, in B.M. Trost and I. Fleming (eds.), Comprehensive Organic Synthesis, Vol. 7, Pergamon Press, Oxford, 1991, p. 449.
4. [2] J. Tsuji, Palladium Reagents and Catalysts - Innovations in Organic Synthesis, Wiley, Chichester, UK, 1995; R.F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; M. Beller, B. Cornils, C.D. Frohning and C.W. Kohlpaintner, J. Mol. Catal., 104 (1995) 17; J. Tsuji, in B.M. Trost and I. Fleming (eds.), Comprehensive Organic Synthesis, Vol. 7, Pergamon Press, Oxford, 1991, p. 449.
5. [2] J. Tsuji, Palladium Reagents and Catalysts - Innovations in Organic Synthesis, Wiley, Chichester, UK, 1995; R.F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; M. Beller, B. Cornils, C.D. Frohning and C.W. Kohlpaintner, J. Mol. Catal., 104 (1995) 17; J. Tsuji, in B.M. Trost and I. Fleming (eds.), Comprehensive Organic Synthesis, Vol. 7, Pergamon Press, Oxford, 1991, p. 449.
6. [3] A. de Meijere and F. Meier, Angew. Chem., 106 (1994) 2473; Angew. Chem., Int. Ed. Engl., 33 (1994) 2379; R.F. Heck, in B.M. Trost and I. Fleming (eds.), Comprehensive Organic Synthesis, Vol. 4, Pergamon Press, Oxford, 1991, p. 833; W. Cabri and I. Candiani, Acc. Chem. Res., 28 (1995) 2; W.A. Herrmann, in B. Cornils and W.A. Herrmann (eds.), Applied Homogeneous Catalysis, VCH, Weinheim, 1996, in press.
7. [3] A. de Meijere and F. Meier, Angew. Chem., 106 (1994) 2473; Angew. Chem., Int. Ed. Engl., 33 (1994) 2379; R.F. Heck, in B.M. Trost and I. Fleming (eds.), Comprehensive Organic Synthesis, Vol. 4, Pergamon Press, Oxford, 1991, p. 833; W. Cabri and I. Candiani, Acc. Chem. Res., 28 (1995) 2; W.A. Herrmann, in B. Cornils and W.A. Herrmann (eds.), Applied Homogeneous Catalysis, VCH, Weinheim, 1996, in press.
8. [3] A. de Meijere and F. Meier, Angew. Chem., 106 (1994) 2473; Angew. Chem., Int. Ed. Engl., 33 (1994) 2379; R.F. Heck, in B.M. Trost and I. Fleming (eds.), Comprehensive Organic Synthesis, Vol. 4, Pergamon Press, Oxford, 1991, p. 833; W. Cabri and I. Candiani, Acc. Chem. Res., 28 (1995) 2; W.A. Herrmann, in B. Cornils and W.A. Herrmann (eds.), Applied Homogeneous Catalysis, VCH, Weinheim, 1996, in press.
9. [3] A. de Meijere and F. Meier, Angew. Chem., 106 (1994) 2473; Angew. Chem., Int. Ed. Engl., 33 (1994) 2379; R.F. Heck, in B.M. Trost and I. Fleming (eds.), Comprehensive Organic Synthesis, Vol. 4, Pergamon Press, Oxford, 1991, p. 833; W. Cabri and I. Candiani, Acc. Chem. Res., 28 (1995) 2; W.A. Herrmann, in B. Cornils and W.A. Herrmann (eds.), Applied Homogeneous Catalysis, VCH, Weinheim, 1996, in press.
10. [3] A. de Meijere and F. Meier, Angew. Chem., 106 (1994) 2473; Angew. Chem., Int. Ed. Engl., 33 (1994) 2379; R.F. Heck, in B.M. Trost and I. Fleming (eds.), Comprehensive Organic Synthesis, Vol. 4, Pergamon Press, Oxford, 1991, p. 833; W. Cabri and I. Candiani, Acc. Chem. Res., 28 (1995) 2; W.A. Herrmann, in B. Cornils and W.A. Herrmann (eds.), Applied Homogeneous Catalysis, VCH, Weinheim, 1996, in press.
11. [4] O. Loiseleur, P. Meier and A. Pfaltz, Angew. Chem., 108 (1996) 218; K. Kondo, M. Sodeoka and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 2453; Y. Sato, M. Mori and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 757; S. Nukui, M. Sodeoka, H. Sasai and M. Shibasaki, J. Org. Chem., 60 (1995) 398; K. Ohrai, K. Kondo, M. Sodeoka and M. Shibasaki, J. Am. Chem. Soc., 116 (1994) 11737; C. Moinet and J.-C. Fiaud, Tetrahedron Lett., 36 (1995) 2051; F. Ozawa, Y. Kobatake, A. Kubo and T. Hayashi, J. Chem. Soc., Chem. Commun., (1994) 1323; L.F. Tietze and R. Schimpf, Angew. Chem., 106 (1994) 1138; Angew. Chem., Int. Ed. Engl., 33 (1994) 1089; S. Sakuraba, K. Awano and K. Achiwa, Synlett, (1994) 291.
12. [4] O. Loiseleur, P. Meier and A. Pfaltz, Angew. Chem., 108 (1996) 218; K. Kondo, M. Sodeoka and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 2453; Y. Sato, M. Mori and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 757; S. Nukui, M. Sodeoka, H. Sasai and M. Shibasaki, J. Org. Chem., 60 (1995) 398; K. Ohrai, K. Kondo, M. Sodeoka and M. Shibasaki, J. Am. Chem. Soc., 116 (1994) 11737; C. Moinet and J.-C. Fiaud, Tetrahedron Lett., 36 (1995) 2051; F. Ozawa, Y. Kobatake, A. Kubo and T. Hayashi, J. Chem. Soc., Chem. Commun., (1994) 1323; L.F. Tietze and R. Schimpf, Angew. Chem., 106 (1994) 1138; Angew. Chem., Int. Ed. Engl., 33 (1994) 1089; S. Sakuraba, K. Awano and K. Achiwa, Synlett, (1994) 291.
13. [4] O. Loiseleur, P. Meier and A. Pfaltz, Angew. Chem., 108 (1996) 218; K. Kondo, M. Sodeoka and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 2453; Y. Sato, M. Mori and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 757; S. Nukui, M. Sodeoka, H. Sasai and M. Shibasaki, J. Org. Chem., 60 (1995) 398; K. Ohrai, K. Kondo, M. Sodeoka and M. Shibasaki, J. Am. Chem. Soc., 116 (1994) 11737; C. Moinet and J.-C. Fiaud, Tetrahedron Lett., 36 (1995) 2051; F. Ozawa, Y. Kobatake, A. Kubo and T. Hayashi, J. Chem. Soc., Chem. Commun., (1994) 1323; L.F. Tietze and R. Schimpf, Angew. Chem., 106 (1994) 1138; Angew. Chem., Int. Ed. Engl., 33 (1994) 1089; S. Sakuraba, K. Awano and K. Achiwa, Synlett, (1994) 291.
14. [4] O. Loiseleur, P. Meier and A. Pfaltz, Angew. Chem., 108 (1996) 218; K. Kondo, M. Sodeoka and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 2453; Y. Sato, M. Mori and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 757; S. Nukui, M. Sodeoka, H. Sasai and M. Shibasaki, J. Org. Chem., 60 (1995) 398; K. Ohrai, K. Kondo, M. Sodeoka and M. Shibasaki, J. Am. Chem. Soc., 116 (1994) 11737; C. Moinet and J.-C. Fiaud, Tetrahedron Lett., 36 (1995) 2051; F. Ozawa, Y. Kobatake, A. Kubo and T. Hayashi, J. Chem. Soc., Chem. Commun., (1994) 1323; L.F. Tietze and R. Schimpf, Angew. Chem., 106 (1994) 1138; Angew. Chem., Int. Ed. Engl., 33 (1994) 1089; S. Sakuraba, K. Awano and K. Achiwa, Synlett, (1994) 291.
15. [4] O. Loiseleur, P. Meier and A. Pfaltz, Angew. Chem., 108 (1996) 218; K. Kondo, M. Sodeoka and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 2453; Y. Sato, M. Mori and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 757; S. Nukui, M. Sodeoka, H. Sasai and M. Shibasaki, J. Org. Chem., 60 (1995) 398; K. Ohrai, K. Kondo, M. Sodeoka and M. Shibasaki, J. Am. Chem. Soc., 116 (1994) 11737; C. Moinet and J.-C. Fiaud, Tetrahedron Lett., 36 (1995) 2051; F. Ozawa, Y. Kobatake, A. Kubo and T. Hayashi, J. Chem. Soc., Chem. Commun., (1994) 1323; L.F. Tietze and R. Schimpf, Angew. Chem., 106 (1994) 1138; Angew. Chem., Int. Ed. Engl., 33 (1994) 1089; S. Sakuraba, K. Awano and K. Achiwa, Synlett, (1994) 291.
16. [4] O. Loiseleur, P. Meier and A. Pfaltz, Angew. Chem., 108 (1996) 218; K. Kondo, M. Sodeoka and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 2453; Y. Sato, M. Mori and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 757; S. Nukui, M. Sodeoka, H. Sasai and M. Shibasaki, J. Org. Chem., 60 (1995) 398; K. Ohrai, K. Kondo, M. Sodeoka and M. Shibasaki, J. Am. Chem. Soc., 116 (1994) 11737; C. Moinet and J.-C. Fiaud, Tetrahedron Lett., 36 (1995) 2051; F. Ozawa, Y. Kobatake, A. Kubo and T. Hayashi, J. Chem. Soc., Chem. Commun., (1994) 1323; L.F. Tietze and R. Schimpf, Angew. Chem., 106 (1994) 1138; Angew. Chem., Int. Ed. Engl., 33 (1994) 1089; S. Sakuraba, K. Awano and K. Achiwa, Synlett, (1994) 291.
17. [4] O. Loiseleur, P. Meier and A. Pfaltz, Angew. Chem., 108 (1996) 218; K. Kondo, M. Sodeoka and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 2453; Y. Sato, M. Mori and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 757; S. Nukui, M. Sodeoka, H. Sasai and M. Shibasaki, J. Org. Chem., 60 (1995) 398; K. Ohrai, K. Kondo, M. Sodeoka and M. Shibasaki, J. Am. Chem. Soc., 116 (1994) 11737; C. Moinet and J.-C. Fiaud, Tetrahedron Lett., 36 (1995) 2051; F. Ozawa, Y. Kobatake, A. Kubo and T. Hayashi, J. Chem. Soc., Chem. Commun., (1994) 1323; L.F. Tietze and R. Schimpf, Angew. Chem., 106 (1994) 1138; Angew. Chem., Int. Ed. Engl., 33 (1994) 1089; S. Sakuraba, K. Awano and K. Achiwa, Synlett, (1994) 291.
18. [4] O. Loiseleur, P. Meier and A. Pfaltz, Angew. Chem., 108 (1996) 218; K. Kondo, M. Sodeoka and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 2453; Y. Sato, M. Mori and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 757; S. Nukui, M. Sodeoka, H. Sasai and M. Shibasaki, J. Org. Chem., 60 (1995) 398; K. Ohrai, K. Kondo, M. Sodeoka and M. Shibasaki, J. Am. Chem. Soc., 116 (1994) 11737; C. Moinet and J.-C. Fiaud, Tetrahedron Lett., 36 (1995) 2051; F. Ozawa, Y. Kobatake, A. Kubo and T. Hayashi, J. Chem. Soc., Chem. Commun., (1994) 1323; L.F. Tietze and R. Schimpf, Angew. Chem., 106 (1994) 1138; Angew. Chem., Int. Ed. Engl., 33 (1994) 1089; S. Sakuraba, K. Awano and K. Achiwa, Synlett, (1994) 291.
19. [4] O. Loiseleur, P. Meier and A. Pfaltz, Angew. Chem., 108 (1996) 218; K. Kondo, M. Sodeoka and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 2453; Y. Sato, M. Mori and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 757; S. Nukui, M. Sodeoka, H. Sasai and M. Shibasaki, J. Org. Chem., 60 (1995) 398; K. Ohrai, K. Kondo, M. Sodeoka and M. Shibasaki, J. Am. Chem. Soc., 116 (1994) 11737; C. Moinet and J.-C. Fiaud, Tetrahedron Lett., 36 (1995) 2051; F. Ozawa, Y. Kobatake, A. Kubo and T. Hayashi, J. Chem. Soc., Chem. Commun., (1994) 1323; L.F. Tietze and R. Schimpf, Angew. Chem., 106 (1994) 1138; Angew. Chem., Int. Ed. Engl., 33 (1994) 1089; S. Sakuraba, K. Awano and K. Achiwa, Synlett, (1994) 291.
20. [4] O. Loiseleur, P. Meier and A. Pfaltz, Angew. Chem., 108 (1996) 218; K. Kondo, M. Sodeoka and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 2453; Y. Sato, M. Mori and M. Shibasaki, Tetrahedron Asymm., 6 (1995) 757; S. Nukui, M. Sodeoka, H. Sasai and M. Shibasaki, J. Org. Chem., 60 (1995) 398; K. Ohrai, K. Kondo, M. Sodeoka and M. Shibasaki, J. Am. Chem. Soc., 116 (1994) 11737; C. Moinet and J.-C. Fiaud, Tetrahedron Lett., 36 (1995) 2051; F. Ozawa, Y. Kobatake, A. Kubo and T. Hayashi, J. Chem. Soc., Chem. Commun., (1994) 1323; L.F. Tietze and R. Schimpf, Angew. Chem., 106 (1994) 1138; Angew. Chem., Int. Ed. Engl., 33 (1994) 1089; S. Sakuraba, K. Awano and K. Achiwa, Synlett, (1994) 291.
21. [5] A. Spencer, J. Organomet. Chem., 258 (1983) 101.
22. [6] W.A. Herrmann, C. Broßmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller and H. Fischer, Angew. Chem., 107 (1995) 1989; Angew. Chem., Int. Ed. Engl., 34 (1995) 1844.
23. [6] W.A. Herrmann, C. Broßmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller and H. Fischer, Angew. Chem., 107 (1995) 1989; Angew. Chem., Int. Ed. Engl., 34 (1995) 1844.
24. [7] M. Beller, H. Fischer, W.A. Hermann, C. Broßmer and K. Öfele, Angew. Chem., 107 (1995) 1992; Angew. Chem., Int. Ed. Engl., 34 (1995) 1848.
25. [7] M. Beller, H. Fischer, W.A. Hermann, C. Broßmer and K. Öfele, Angew. Chem., 107 (1995) 1992; Angew. Chem., Int. Ed. Engl., 34 (1995) 1848.
26. [8] M. Beller, T. Riermeier and W.A. Herrmann, unpublished results.
27. [9] G. Schmid, Clusters and Colloids, VCH, Weinheim, 1994; G. Schmid, Chem. Rev., 92 (1992) 1709; M.T. Reetz and W. Helbig, J. Am. Chem. Soc., 116 (1994) 7401; M.T. Reetz and S.A. Quaiser, Angew. Chem., 107 (1995) 2461; Angew. Chem., Int. Ed. Engl., 34 (1995) 2240.
28. [9] G. Schmid, Clusters and Colloids, VCH, Weinheim, 1994; G. Schmid, Chem. Rev., 92 (1992) 1709; M.T. Reetz and W. Helbig, J. Am. Chem. Soc., 116 (1994) 7401; M.T. Reetz and S.A. Quaiser, Angew. Chem., 107 (1995) 2461; Angew. Chem., Int. Ed. Engl., 34 (1995) 2240.
29. [9] G. Schmid, Clusters and Colloids, VCH, Weinheim, 1994; G. Schmid, Chem. Rev., 92 (1992) 1709; M.T. Reetz and W. Helbig, J. Am. Chem. Soc., 116 (1994) 7401; M.T. Reetz and S.A. Quaiser, Angew. Chem., 107 (1995) 2461; Angew. Chem., Int. Ed. Engl., 34 (1995) 2240.
30. [9] G. Schmid, Clusters and Colloids, VCH, Weinheim, 1994; G. Schmid, Chem. Rev., 92 (1992) 1709; M.T. Reetz and W. Helbig, J. Am. Chem. Soc., 116 (1994) 7401; M.T. Reetz and S.A. Quaiser, Angew. Chem., 107 (1995) 2461; Angew. Chem., Int. Ed. Engl., 34 (1995) 2240.
31. [9] G. Schmid, Clusters and Colloids, VCH, Weinheim, 1994; G. Schmid, Chem. Rev., 92 (1992) 1709; M.T. Reetz and W. Helbig, J. Am. Chem. Soc., 116 (1994) 7401; M.T. Reetz and S.A. Quaiser, Angew. Chem., 107 (1995) 2461; Angew. Chem., Int. Ed. Engl., 34 (1995) 2240.
32. [10] A. Behr and H. Schmidke, Chem. Ing. Tech., 65 (1993) 568; H. Bönnemann, W. Brijoux, R. Brinkmann, E. Dinjus, R. Fretzen, T. Joußen and B. Korall, J. Mol. Catal., 74 (1992) 323; L.N. Lewis, R.J. Uriarte and N. Lewis, J. Catal., 127 (1991) 67; J. Richter, Ph.D. Thesis, Essen, 1994.
33. [10] A. Behr and H. Schmidke, Chem. Ing. Tech., 65 (1993) 568; H. Bönnemann, W. Brijoux, R. Brinkmann, E. Dinjus, R. Fretzen, T. Joußen and B. Korall, J. Mol. Catal., 74 (1992) 323; L.N. Lewis, R.J. Uriarte and N. Lewis, J. Catal., 127 (1991) 67; J. Richter, Ph.D. Thesis, Essen, 1994.
34. [10] A. Behr and H. Schmidke, Chem. Ing. Tech., 65 (1993) 568; H. Bönnemann, W. Brijoux, R. Brinkmann, E. Dinjus, R. Fretzen, T. Joußen and B. Korall, J. Mol. Catal., 74 (1992) 323; L.N. Lewis, R.J. Uriarte and N. Lewis, J. Catal., 127 (1991) 67; J. Richter, Ph.D. Thesis, Essen, 1994.
35. [10] A. Behr and H. Schmidke, Chem. Ing. Tech., 65 (1993) 568; H. Bönnemann, W. Brijoux, R. Brinkmann, E. Dinjus, R. Fretzen, T. Joußen and B. Korall, J. Mol. Catal., 74 (1992) 323; L.N. Lewis, R.J. Uriarte and N. Lewis, J. Catal., 127 (1991) 67; J. Richter, Ph.D. Thesis, Essen, 1994.
36. [11] L.A. Fowley, D. Michos, X.-L. Luo and R.H. Crabtree, Tetrahedron Lett., 34 (1993) 3075.
37. [12] H. Bönnemann, W. Brijoux, R. Brinkmann, E. Dinjus, R. Fretzen, T. Joußen and B. Korall, Angew. Chem., 103 (1991) 1344; Angew. Chem., Int. Ed. Engl., 30 (1991) 1312; H. Bönnemann, W. Brijoux and T. Joussen, Angew. Chem., 103 (1991) 1344; Angew. Chem., Int. Ed. Engl., 29 (1990) 273.
38. [12] H. Bönnemann, W. Brijoux, R. Brinkmann, E. Dinjus, R. Fretzen, T. Joußen and B. Korall, Angew. Chem., 103 (1991) 1344; Angew. Chem., Int. Ed. Engl., 30 (1991) 1312; H. Bönnemann, W. Brijoux and T. Joussen, Angew. Chem., 103 (1991) 1344; Angew. Chem., Int. Ed. Engl., 29 (1990) 273.
39. [12] H. Bönnemann, W. Brijoux, R. Brinkmann, E. Dinjus, R. Fretzen, T. Joußen and B. Korall, Angew. Chem., 103 (1991) 1344; Angew. Chem., Int. Ed. Engl., 30 (1991) 1312; H. Bönnemann, W. Brijoux and T. Joussen, Angew. Chem., 103 (1991) 1344; Angew. Chem., Int. Ed. Engl., 29 (1990) 273.
40. [12] H. Bönnemann, W. Brijoux, R. Brinkmann, E. Dinjus, R. Fretzen, T. Joußen and B. Korall, Angew. Chem., 103 (1991) 1344; Angew. Chem., Int. Ed. Engl., 30 (1991) 1312; H. Bönnemann, W. Brijoux and T. Joussen, Angew. Chem., 103 (1991) 1344; Angew. Chem., Int. Ed. Engl., 29 (1990) 273.
41. [13] T. Jeffrey, Tetrahedron Lett., 35 (1994) 3051; O. Reiser, B. König, K. Meerbolz, J. Heinze, T. Wallauer, F. Gerson, B. Frim, M. Rabinovitz and A. de Meijere, J. Am. Chem. Soc., 115 (1993) 3511; T. Jeffrey, Tetrahedron Lett., 26 (1985) 2667.
42. [13] T. Jeffrey, Tetrahedron Lett., 35 (1994) 3051; O. Reiser, B. König, K. Meerbolz, J. Heinze, T. Wallauer, F. Gerson, B. Frim, M. Rabinovitz and A. de Meijere, J. Am. Chem. Soc., 115 (1993) 3511; T. Jeffrey, Tetrahedron Lett., 26 (1985) 2667.
43. [13] T. Jeffrey, Tetrahedron Lett., 35 (1994) 3051; O. Reiser, B. König, K. Meerbolz, J. Heinze, T. Wallauer, F. Gerson, B. Frim, M. Rabinovitz and A. de Meijere, J. Am. Chem. Soc., 115 (1993) 3511; T. Jeffrey, Tetrahedron Lett., 26 (1985) 2667.