A Practical Recycle of a Ligand-Free Palladium Catalyst for Heck Reactions

Advanced Synthesis and Catalysis

Volumn 344, Issue 9, 2002, Pages 996-1002

  De Vries, André H M ^a   Parlevliet, Floris J ^a   Schmieder van De Vondervoort, Lizette ^a   Mommers, John H M ^b   Henderickx, Huub J W ^b   Walet, Monique A M ^b   De Vries, Johannes G ^a  

^a DSM Fine Chemicals Austria Nfg GmbH & Co KG   (Netherlands)

^b DSM RESEARCH   (Netherlands)

Author keywords

Catalyst recovery; Heck reaction; Iodine; Ligand free; Palladium; Re activation

Indexed keywords

EID: 0012356884     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200210)344:9<996::AID-ADSC996>3.0.CO;2-J     Document Type: Article

References (47)

1. a) Transition Metals for Organic Synthesis, (Eds.: M. Beller, C. Bolm), Wiley, Weinheim, 1998;
2. b) Comprehensive Asymmetric Catalysis, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999.
3. Applied Homogeneous Catalysis with Organometallic Compounds, (Eds.: B. Cornils, W. A. Herrmann), Wiley, Weinheim, 1996.
4. H. U. Blaser, F. Spindler, M. Studer, Appl. Cat. A, 2001, 221, 119.
5. a) J. G. de Vries, Can. J. Chem. 2001, 79, 1086;
6. b) C. E. Tucker, J. G. de Vries, Topics in Catalysis 2002, 19, 111.
7. a) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009;
8. b) N. J. Whitcombe, K. K. (M.) Hii, S. E. Gibson, Tetrahedron 2001, 57, 7449.
9. a) W. A. Herrmann, M. Elison, J. Fischer, C. Köchler, G. R. J. Artus, Angew. Chem. Int. Ed. 1995, 34, 2371;
10. b) M. T. Reetz, E. Westermann, R. Lohmer, G. Lohmer, Tetrahedron Lett. 1998, 39, 8449;
11. c) M. Ohff, A. Ohff, D. Milstein Chem. Commun. 1999, 357;
12. d) A. S. Gruber, D. Zim, G. Ebeling, A. L. Monteiro, J. Dupont, Org. Lett. 2000, 2, 1287;
13. e) D. A. Alonso, C. Nájera, M. C. Pacheco, Org. Lett. 2000, 2, 1823;
14. f) I. P. Beletskaya, A. N. Kashin, N.B. Karlstedt, A. V. Mitin, A. V. Cheprakov, G. M. Kazankov, J. Organomet. Chem. 2001, 622, 89.
15. a) T. Jeffery, Synthesis 1987, 70;
16. b) T. Jeffery, Tetrahedron 1996, 52, 10113;
17. c) T. Jeffery, in Advances in Metal-Organic Chemistry, (Ed.: L. S. Liebeskind), JAI Press, Greenwich, 1996, Vol. 5 p. 153;
18. d) C. Gürtler, S. L. Buchwald, Chem. Eur. J. 1999, 5, 3107.
19. a) N. A. Bumagin, P. G. More, I. P. Beletskaya, J. Organomet. Chem. 1989, 371, 397;
20. b) N. A. Bumagin, V. V. Bykov, L. I. Sukhomlinova, T. P. Tolstaya, I. P. Beletskaya, J. Organomet. Chem. 1995, 486, 259;
21. c) I. P. Beletskaya, Pure Appl. Chem. 1997, 69, 471.
22. a) M. T. Reetz, G. Lohmer, Chem. Commun. 1996, 1921;
23. b) M. Beller, H. Fischer, K. Kühlein, C.-P. Reisinger, W. A. Herrmann, J. Organomet. Chem. 1996, 520, 257;
24. c) M. T. Reetz, E. Westermann, Angew. Chem. Int. Ed. 2000, 39, 165.
25. a) K. Kikukawa, K. Maemura, Y. Kiseki, F. Wada, T. Matsuda, J. Org. Chem. 1981, 46, 4885;
26. b) S. Sengupta, S. Bhattacharya, J. Chem. Soc. Perkin Trans. 1 1993, 1943;
27. c) M. Beller, H. Fischer, K. Kühlein, Tetrahedron Lett. 1994, 35, 8773;
28. d) M. Beller, K. Kühlein, Synlett 1995, 441.
29. a) H. U. Blaser, A. Spencer, J. Organomet. Chem. 1982, 233, 267;
30. b) A. Spencer, J. Organomet. Chem. 1983, 247, 117.
31. M. Stephan, A. J. J. M. Teunissen, G. K. M. Verzijl, J. G. de Vries, Angew. Chem. Int. Ed. 1998, 37, 662.
32. For a recent review on catalyst product separation techniques in Heck reactions, see: B. M. Bhanage, M. Arai, Catalysis Reviews 2001, 43, 315.
33. a) A. Eisenstadt, in Catalysis of Organic Reactions, (Ed.: F. E. Herkes), Chemical Industries, 1998, p. 415;
34. b) V. M. Wall, A. Eisenstadt, D. J Ager, S. A. Laneman, Platinum Metals Rev. 1999, 43, 138.
35. c) F. Zhao, B. M. Bhanage, M. Shirai, M. Arai, Chem. Eur. J. 2000, 6, 843 and references therein.
36. a) A. Biffis, M. Zecca, M. Basato, Eur. J. Inorg. Chem. 2001, 1131;
37. b) K. Köhler, R. G. Heidenreich, J. G. E. Krauter, J. Pietsch, Chem. Eur. J. 2002, 8, 622.
38. a) C. P. Mehnert, D. W. Weaver, J. Y. Ying, J. Am. Chem. Soc. 1998, 120, 12289;
39. b) A. Wali, S. Muthukumaru Pillai, V. Kaushik, S. Satish, Appl. Catal. A 1996, 135, 83;
40. c) L. Djakovitch, K. Köhler, J. Am. Chem. Soc. 2001, 123, 5990.
41. 2, but at 140°C: M. Qadir, T. Möchel, K. K. (M) Hii, Tetrahedron 2000, 56, 7975.
42. F. J. Parlevliet, A. H. M. de Vries, J. G. de Vries, (DSM nv), WO 02/00340, 2002; Chem. Abstr. 2002, 555436.
43. The separated reaction mixtures contained between 5-10 ppm palladium indicating a small level of leaching of the palladium (2-3% in every run).
44. A manuscript is in preparation describing our detailed study on ligand-free Heck reactions between a wide range of aryl bromides (activated, non-activated and de-activated) and several olefins (electron deficient and electron rich). Aryl chlorides were not reactive at all using this ligand-free palladium catalysts.
45. Gmelins Handbuch der Anorganischen Chemie, (Ed.: E. Pietsch), Verlag Chemie, Berlin, 1942, system nummer 65, p. 288.
46. C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314
47. Recently similar palladium species were detected by using EXAFS in the phosphine-free Heck reaction between iodobenzene and 2-methylprop-2-en-1-ol: J. Evans, L. O'Neill, V. L. Kambhampati, G. Rayner, S. Turin, A. Genge, A. J. Dent, T. Neisus, J. Chem. Soc. Dalton Trans. 2002, 2207.