An iminophosphine dendrimeric ligand and its evaluation in the Heck reaction

Tetrahedron Letters

Volumn 44, Issue 24, 2003, Pages 4575-4578

  Catsoulacos, Dimitrios P ^a   Steele, Barry R ^a   Heropoulos, Georgios A ^a   Micha Screttas, Maria ^a   Screttas, Constantinos G ^a  

^a INSTITUTE OF BIOLOGY   (Greece)

Author keywords

Catalysis; Dendrimer; Heck reaction; Palladium complex; Phosphine

Indexed keywords

ACETIC ACID; AMINE; PALLADIUM; PHOSPHINE DERIVATIVE;

ARTICLE; ELECTRON; EVALUATION; HECK REACTION; MOLECULAR INTERACTION;

EID: 0037727900     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00983-3     Document Type: Article

References (43)

1. Astruc D., Chardac F. Chem. Rev. 101:2001;2991.
2. Oostrom G.E., Reek J.N.H., Kamer P.C.J., van Leeuwen P.W.N.M. Angew. Chem., Int. Ed. 40:2001;1828.
3. Ropartz L., Morris R.E., Foster D.F., Cole-Hamilton D.J. Chem. Commun. 2001;361.
4. Oosterom G.E., van Haaren R.J., Reek J.N.H., Kamer P.C.J., van Leeuwen P.W.N.M. Chem. Commun. 1999;1119.
5. De Groot D., Emmerink P.G., Coucke C., Reek J.N.H., Kamer P.C.J., van Leeuwen P.W.N.M. Inorg. Chem. Commun. 3:2000;711.
6. Brinkmann N., Giebel D., Lohmer G., Reetz M.T., Kragl U. J. Catal. 183:1999;163.
7. Arya P., Panda G., Rao N.V., Alper H., Bourque S.C., Manzer L.E. J. Am. Chem. Soc. 123:2001;2889.
8. Arya P., Rao N.V., Singkhonrat J., Alper H., Bourque S.C., Manzer L.E. J. Org. Chem. 65:2000;1881.
9. Bourque S.C., Maltais F., Xiao W.J., Tardif O., Alper H., Manzer L.E., Arya P. J. Am. Chem. Soc. 121:1999;3035.
10. Alper H., Arya P., Bourque C.S., Jefferson G.R., Manzer L.E. Can. J. Chem. 78:2000;920.
11. Fan Q.-H., Chen X.-M., Jiang D.-Z., Xi F., Chan A.S.C. Chem. Commun. 2000;789.
12. Petrucci-Samija M., Guillemette V., Dasgupta M., Kakkar A.K. J. Am. Chem. Soc. 121:1999;1968.
13. Gong A., Fan Q., Chen Y., Liu C., Xi F. J. Mol. Catal. 159:2000;225.
14. Reetz M.T., Lohmer G., Schwickardi R. Angew. Chem., Int. Ed. Engl. 36:1997;1526.
15. Mizugaki T., Ooe M., Ebitani K., Kaneda K. J. Mol. Catal. A. 145:1999;329.
16. Mizugaki T., Murata M., Ooe M., Ebitani K., Kaneda K. Chem. Commun. 2002;52.
17. Hovestad N.J., Eggeling E.B., Heidbüchel H.J., Jastrzebski J.T.B.H., Kragl U., Keim W., Vogt D., van Koten G. Angew. Chem., Int. Ed. 38:1999;1655.
18. Newkome G.R., Moorefield C.N., Vögtle F. Dendritic Molecules: Concepts, Syntheses and Perspectives. 1996;VCH, New York.
19. Janssen H.M., Meijer E.W. Chem. Rev. 99:1999;1665.
20. Piotti M.E., Rivere F. Jr., Bond R., Hawker C.J., Fréchet J.M. J. Am. Chem. Soc. 121:1999;9471.
21. For positive dendritic effects, see: (a) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 707; (b) Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. Engl. 2001, 40, 1828; (c) Brunner, H. J. Organomet. Chem. 1995, 500, 39; (d) Breinbauer, R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 3604; (e) Butz, T.; Murer, P.; Seebach, D. Polym. Pater. Sci. Eng. 1997, 77, 132; (f) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. Engl. 2001, 40, 92; (g) Francavilla, C.; Drake, M. D.; Bright, F. V.; Detty, M. R. J. Am. Chem. Soc. 2001, 123, 57; for negative dendritic effects, see: (h) Peerlings, H. W. I.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1563; (i) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. 2000, 39, 176.
22. For positive dendritic effects, see: (a) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 707; (b) Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. Engl. 2001, 40, 1828; (c) Brunner, H. J. Organomet. Chem. 1995, 500, 39; (d) Breinbauer, R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 3604; (e) Butz, T.; Murer, P.; Seebach, D. Polym. Pater. Sci. Eng. 1997, 77, 132; (f) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. Engl. 2001, 40, 92; (g) Francavilla, C.; Drake, M. D.; Bright, F. V.; Detty, M. R. J. Am. Chem. Soc. 2001, 123, 57; for negative dendritic effects, see: (h) Peerlings, H. W. I.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1563; (i) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. 2000, 39, 176.
23. For positive dendritic effects, see: (a) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 707; (b) Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. Engl. 2001, 40, 1828; (c) Brunner, H. J. Organomet. Chem. 1995, 500, 39; (d) Breinbauer, R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 3604; (e) Butz, T.; Murer, P.; Seebach, D. Polym. Pater. Sci. Eng. 1997, 77, 132; (f) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. Engl. 2001, 40, 92; (g) Francavilla, C.; Drake, M. D.; Bright, F. V.; Detty, M. R. J. Am. Chem. Soc. 2001, 123, 57; for negative dendritic effects, see: (h) Peerlings, H. W. I.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1563; (i) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. 2000, 39, 176.
24. For positive dendritic effects, see: (a) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 707; (b) Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. Engl. 2001, 40, 1828; (c) Brunner, H. J. Organomet. Chem. 1995, 500, 39; (d) Breinbauer, R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 3604; (e) Butz, T.; Murer, P.; Seebach, D. Polym. Pater. Sci. Eng. 1997, 77, 132; (f) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. Engl. 2001, 40, 92; (g) Francavilla, C.; Drake, M. D.; Bright, F. V.; Detty, M. R. J. Am. Chem. Soc. 2001, 123, 57; for negative dendritic effects, see: (h) Peerlings, H. W. I.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1563; (i) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. 2000, 39, 176.
25. For positive dendritic effects, see: (a) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 707; (b) Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. Engl. 2001, 40, 1828; (c) Brunner, H. J. Organomet. Chem. 1995, 500, 39; (d) Breinbauer, R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 3604; (e) Butz, T.; Murer, P.; Seebach, D. Polym. Pater. Sci. Eng. 1997, 77, 132; (f) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. Engl. 2001, 40, 92; (g) Francavilla, C.; Drake, M. D.; Bright, F. V.; Detty, M. R. J. Am. Chem. Soc. 2001, 123, 57; for negative dendritic effects, see: (h) Peerlings, H. W. I.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1563; (i) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. 2000, 39, 176.
26. For positive dendritic effects, see: (a) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 707; (b) Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. Engl. 2001, 40, 1828; (c) Brunner, H. J. Organomet. Chem. 1995, 500, 39; (d) Breinbauer, R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 3604; (e) Butz, T.; Murer, P.; Seebach, D. Polym. Pater. Sci. Eng. 1997, 77, 132; (f) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. Engl. 2001, 40, 92; (g) Francavilla, C.; Drake, M. D.; Bright, F. V.; Detty, M. R. J. Am. Chem. Soc. 2001, 123, 57; for negative dendritic effects, see: (h) Peerlings, H. W. I.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1563; (i) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. 2000, 39, 176.
27. For positive dendritic effects, see: (a) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 707; (b) Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. Engl. 2001, 40, 1828; (c) Brunner, H. J. Organomet. Chem. 1995, 500, 39; (d) Breinbauer, R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 3604; (e) Butz, T.; Murer, P.; Seebach, D. Polym. Pater. Sci. Eng. 1997, 77, 132; (f) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. Engl. 2001, 40, 92; (g) Francavilla, C.; Drake, M. D.; Bright, F. V.; Detty, M. R. J. Am. Chem. Soc. 2001, 123, 57; for negative dendritic effects, see: (h) Peerlings, H. W. I.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1563; (i) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. 2000, 39, 176.
28. For positive dendritic effects, see: (a) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 707; (b) Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. Engl. 2001, 40, 1828; (c) Brunner, H. J. Organomet. Chem. 1995, 500, 39; (d) Breinbauer, R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 3604; (e) Butz, T.; Murer, P.; Seebach, D. Polym. Pater. Sci. Eng. 1997, 77, 132; (f) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. Engl. 2001, 40, 92; (g) Francavilla, C.; Drake, M. D.; Bright, F. V.; Detty, M. R. J. Am. Chem. Soc. 2001, 123, 57; for negative dendritic effects, see: (h) Peerlings, H. W. I.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1563; (i) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. 2000, 39, 176.
29. For positive dendritic effects, see: (a) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 707; (b) Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. Engl. 2001, 40, 1828; (c) Brunner, H. J. Organomet. Chem. 1995, 500, 39; (d) Breinbauer, R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 3604; (e) Butz, T.; Murer, P.; Seebach, D. Polym. Pater. Sci. Eng. 1997, 77, 132; (f) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. Engl. 2001, 40, 92; (g) Francavilla, C.; Drake, M. D.; Bright, F. V.; Detty, M. R. J. Am. Chem. Soc. 2001, 123, 57; for negative dendritic effects, see: (h) Peerlings, H. W. I.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1563; (i) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. 2000, 39, 176.
30. Alonso E., Astruc D. J. Am. Chem. Soc. 122:2000;3222.
31. 3): δ -13.82 (major: anti), -11.62 (minor: syn or occluded starting o-diphenylphosphinobenzaldehyde).
32. Udenfriend S., Stein S., Böhlen P., Dairman W., Leimgruber W., Weigele M. Science. 178:1972;871.
33. Antonaroli S., Crociani B. J. Organomet. Chem. 560:1998;137.
34. Frohning, C. D.; Kohlpainter, C. W. In Applied Homogeneous Catalysis with Organometallic Compounds, Cornils, B.; Herrmann, W. A., Eds.; VCH, Weinheim, 1996; Vol. 1, Chapter 2.1.
35. Peori M.B., Kakkar A.K. Organometallics. 22:2002;1788.
36. Whitcombe N.J., Hii K.K., Gibson S.E. Tetrahedron. 57:2001;7449.
37. Koprowski M., Sebastián R.-M., Maraval V., Zablocka M., Cadierno V., Donnadieu B., Igau A., Caminade A.-M., Majoral J.-P. J. Am. Chem. Soc. 21:2002;4680.
38. This mixture forms two layers at room temperature, which coalesce at temperatures roughly above 50°C.
39. 2OH.
40. Chauvin Y., Mussmann L., Olivier H. Angew. Chem., Int. Ed. Engl. 107:1995;2941.
41. Beletskaya I.P., Cheprakov A. Chem. Rev. 100:2000;3066.
42. The syntheses of the iminophosphines, 3 and 4, were carried out by reaction of 2-diphenylphosphinobenzaldehyde with n-hexylamine and 2,6-bis(3-pentyl)aniline (see Ref. 19), respectively, in methanol in the presence of a catalytic quantity of formic acid.
43. Steele B.R., Micha-Screttas M., Screttas C.G. Appl. Organomet. Chem. 16:2002;501.