An easily accessible resin-supported palladium catalyst for Sonogashira coupling

Synlett

Volumn , Issue 7, 2003, Pages 1049-1051

  Gonthier, Elisabeth ^a   Breinbauer, Rolf ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Catalyst; Combinatorial chemistry; Cross coupling; Palladium; Solid phase

Indexed keywords

PALLADIUM; PHOSPHINE; POLYMER; POLYSTYRENE DERIVATIVE; REAGENT; RESIN;

ARTICLE; CATALYSIS; CATALYST; CHELATION; CHEMICAL REACTION; SYNTHESIS;

EID: 0037561597     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39305     Document Type: Article

References (30)

1. For leading reviews see:.(a) Kirschnig, A.; Monenschein, H.; Wittenberg, R. Angew. Chem. Int. Ed. 2001, 40, 650.. (b) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815..(c) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320..(d) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101.
2. For leading reviews see:.(a) Kirschnig, A.; Monenschein, H.; Wittenberg, R. Angew. Chem. Int. Ed. 2001, 40, 650.. (b) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815..(c) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320..(d) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101.
3. For leading reviews see:.(a) Kirschnig, A.; Monenschein, H.; Wittenberg, R. Angew. Chem. Int. Ed. 2001, 40, 650.. (b) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815..(c) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320..(d) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101.
4. For leading reviews see:.(a) Kirschnig, A.; Monenschein, H.; Wittenberg, R. Angew. Chem. Int. Ed. 2001, 40, 650.. (b) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815..(c) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320..(d) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101.
5. Recent reviews:.(a) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275..(b) Clapham, B.; Reger, T. S.; Janda, K. D. Tetrahedron 2001, 57, 4637.. (c) de Miguel, Y. R.; Brule, E.; Margue, R. G. J. Chem. Soc., Perkin Trans. 1 2001, 3085.
6. Recent reviews:.(a) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275..(b) Clapham, B.; Reger, T. S.; Janda, K. D. Tetrahedron 2001, 57, 4637.. (c) de Miguel, Y. R.; Brule, E.; Margue, R. G. J. Chem. Soc., Perkin Trans. 1 2001, 3085.
7. Recent reviews:.(a) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275..(b) Clapham, B.; Reger, T. S.; Janda, K. D. Tetrahedron 2001, 57, 4637.. (c) de Miguel, Y. R.; Brule, E.; Margue, R. G. J. Chem. Soc., Perkin Trans. 1 2001, 3085.
8. For example:.(a) Mizugaki, T.; Murata, M.; Ooe, M.; Ebitani, K.; Kaneda, K. Chem. Commun. 2002, 52..(b) La Pointe, A. M. J. Comb. Chem. 1999, 1, 101..(c) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526..(d) Reetz, M. T.; Waldvogel, S. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 865.
9. For example:.(a) Mizugaki, T.; Murata, M.; Ooe, M.; Ebitani, K.; Kaneda, K. Chem. Commun. 2002, 52..(b) La Pointe, A. M. J. Comb. Chem. 1999, 1, 101..(c) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526..(d) Reetz, M. T.; Waldvogel, S. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 865.
10. For example:.(a) Mizugaki, T.; Murata, M.; Ooe, M.; Ebitani, K.; Kaneda, K. Chem. Commun. 2002, 52..(b) La Pointe, A. M. J. Comb. Chem. 1999, 1, 101..(c) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526..(d) Reetz, M. T.; Waldvogel, S. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 865.
11. For example:.(a) Mizugaki, T.; Murata, M.; Ooe, M.; Ebitani, K.; Kaneda, K. Chem. Commun. 2002, 52..(b) La Pointe, A. M. J. Comb. Chem. 1999, 1, 101..(c) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526..(d) Reetz, M. T.; Waldvogel, S. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 865.
12. (a) Reetz, M. T.; Becker, M. unpublished results..
13. (b) Becker, M. Diplomarbeit; Universität: Marburg, 1997..
14. (c) Arya, P.; Panda, G.; Rao, N. V.; Alper, H.; Bourque, S. C.; Manzer, L. E. J. Am. Chem. Soc. 2001, 123, 2889..
15. (d) Hudkins, C. M. G.; Knights, K. A.; Johnson, B. F. G.; de Miguel, Y. R.; Raja, R.; Thomas, J. M. Chem. Commun. 2001, 2624..
16. (e) Kayaki, Y.; Shimokawatoko, Y.; Ikariya, T. Adv. Synth. Catal. 2003, 345, 175.
17. 2 applying a similar strategy:. (a) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997..(b) Uozumi, Y.; Kimura, T. Synlett 2002, 2045..(c) Palladium complexes immobilized on dendrimer modified silica and their application in the Heck reaction have also been reported: Alper, H.; Prabhat, A.; Bourque, S. C.; Jefferson, G. R.; Manzer, L. E. Can. J. Chem. 2000, 78, 920.
18. 2 applying a similar strategy:. (a) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997..(b) Uozumi, Y.; Kimura, T. Synlett 2002, 2045..(c) Palladium complexes immobilized on dendrimer modified silica and their application in the Heck reaction have also been reported: Alper, H.; Prabhat, A.; Bourque, S. C.; Jefferson, G. R.; Manzer, L. E. Can. J. Chem. 2000, 78, 920.
19. 2 applying a similar strategy:. (a) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997..(b) Uozumi, Y.; Kimura, T. Synlett 2002, 2045..(c) Palladium complexes immobilized on dendrimer modified silica and their application in the Heck reaction have also been reported: Alper, H.; Prabhat, A.; Bourque, S. C.; Jefferson, G. R.; Manzer, L. E. Can. J. Chem. 2000, 78, 920.
20. 2 (2x). The beads are dried in vacuo until the weight remains constant. We have successfully applied this procedure for the preparation of 3 using several types of polystyrene resins (varying in grain size, degree of cross-linking, and loading), Tentagel-resin, and macroporous beads.
21. 2 (3 x 40 mL). The beads are dried in vacuo until the weight remains constant. Elemental analysis: 0.81% N, 3.22% P, 5.72% Pd (elemental analyses have been carried out by Mikroanalytisches Laboratorium H. Kolbe, Mülheim/Ruhr).
22. Tsuji, J. Palladium Reagents: Innovations in Organic Synthesis; Wiley: New York, 1998.
23. (a) Uozumi, Y.; Kobayahsi, Y. Heterocycles 2003, 29, 1255..
24. (b) Leese, M. P.; Williams, J. M. J. Synlett 1999, 1645..
25. (c) Cai, M.-Z.; Song, C.-S.; Huang, X. Synth. Commun. 1997, 27, 1935..
26. (d) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843..
27. (e) Villemin, D.; Goussu, D. Heterocycles 1989, 29, 1255..
28. (f) Terasawa, M.; Kaneda, K.; Imanaka, T.; Teranishi, S. J. Organomet. Chem. 1978, 162, 403.
29. 2, pentane) provided 265.2 mg 7a (99%, colorless crystals).
30. Polymeric bound Pd catalyst 4 can be stored for several months without any significant loss of activity (Schlenk flask, argon, 4°C).