Chloropalladated propargyl amine: A highly efficient phosphine-free catalyst precursor for the Heck reaction

Organic Letters

Volumn 5, Issue 7, 2003, Pages 983-986

  Consorti, Crestina S ^a   Zanini, Mara L ^a   Leal, Sheila ^a   Ebeling, Gunter ^a   Dupont, Jaïrton ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; AMINE; BROMINE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; STYRENE DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; HECK REACTION; ROOM TEMPERATURE; TEMPERATURE DEPENDENCE; TRANSMISSION ELECTRON MICROSCOPY;

EID: 0141630304     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027337l     Document Type: Article

References (32)

1. For recent reviews, see: (a) Dupont, J.; Pfeffer, M.; Spencer, J. Eur. J. Inorg. Chem. 2001, 1917-1927. (b) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750-3781. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rep. 2000, 100, 3009-3066.
2. For recent reviews, see: (a) Dupont, J.; Pfeffer, M.; Spencer, J. Eur. J. Inorg. Chem. 2001, 1917-1927. (b) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750-3781. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rep. 2000, 100, 3009-3066.
3. For recent reviews, see: (a) Dupont, J.; Pfeffer, M.; Spencer, J. Eur. J. Inorg. Chem. 2001, 1917-1927. (b) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750-3781. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rep. 2000, 100, 3009-3066.
4. Herrmann, W. A.; Brossmer, C.; Ofele, K.; Reisinger, C. P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844-1848.
5. See for example: (a) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357-358. (b) Zim, D.; Gruber, A. S.; Ebeling, G.; Dupont, J.; Monteiro, A. L. Org. Lett. 2000, 2, 2881-2884. (c) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058-9064. (d) Munoz, M. P.; Martin-Matute, B.; Fernandez-Rivas, C.; Cardenas, D. J.; Echavarren, A. M. Adv. Synth. Catal. 2001, 343, 338-342. (e) Alonso, D. A.; Najera, C.; Pacheco, M. C. Adv. Synth. Catal. 2002, 344, 172-183. (f) Morales-Morales, D.; Redon, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619-1620. (g) Albisson, D. A.; Bedford, R. B.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793-9796.
6. See for example: (a) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357-358. (b) Zim, D.; Gruber, A. S.; Ebeling, G.; Dupont, J.; Monteiro, A. L. Org. Lett. 2000, 2, 2881-2884. (c) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058-9064. (d) Munoz, M. P.; Martin-Matute, B.; Fernandez-Rivas, C.; Cardenas, D. J.; Echavarren, A. M. Adv. Synth. Catal. 2001, 343, 338-342. (e) Alonso, D. A.; Najera, C.; Pacheco, M. C. Adv. Synth. Catal. 2002, 344, 172-183. (f) Morales-Morales, D.; Redon, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619-1620. (g) Albisson, D. A.; Bedford, R. B.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793-9796.
7. See for example: (a) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357-358. (b) Zim, D.; Gruber, A. S.; Ebeling, G.; Dupont, J.; Monteiro, A. L. Org. Lett. 2000, 2, 2881-2884. (c) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058-9064. (d) Munoz, M. P.; Martin-Matute, B.; Fernandez-Rivas, C.; Cardenas, D. J.; Echavarren, A. M. Adv. Synth. Catal. 2001, 343, 338-342. (e) Alonso, D. A.; Najera, C.; Pacheco, M. C. Adv. Synth. Catal. 2002, 344, 172-183. (f) Morales-Morales, D.; Redon, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619-1620. (g) Albisson, D. A.; Bedford, R. B.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793-9796.
8. See for example: (a) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357-358. (b) Zim, D.; Gruber, A. S.; Ebeling, G.; Dupont, J.; Monteiro, A. L. Org. Lett. 2000, 2, 2881-2884. (c) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058-9064. (d) Munoz, M. P.; Martin-Matute, B.; Fernandez-Rivas, C.; Cardenas, D. J.; Echavarren, A. M. Adv. Synth. Catal. 2001, 343, 338-342. (e) Alonso, D. A.; Najera, C.; Pacheco, M. C. Adv. Synth. Catal. 2002, 344, 172-183. (f) Morales-Morales, D.; Redon, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619-1620. (g) Albisson, D. A.; Bedford, R. B.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793-9796.
9. See for example: (a) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357-358. (b) Zim, D.; Gruber, A. S.; Ebeling, G.; Dupont, J.; Monteiro, A. L. Org. Lett. 2000, 2, 2881-2884. (c) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058-9064. (d) Munoz, M. P.; Martin-Matute, B.; Fernandez-Rivas, C.; Cardenas, D. J.; Echavarren, A. M. Adv. Synth. Catal. 2001, 343, 338-342. (e) Alonso, D. A.; Najera, C.; Pacheco, M. C. Adv. Synth. Catal. 2002, 344, 172-183. (f) Morales-Morales, D.; Redon, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619-1620. (g) Albisson, D. A.; Bedford, R. B.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793-9796.
10. See for example: (a) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357-358. (b) Zim, D.; Gruber, A. S.; Ebeling, G.; Dupont, J.; Monteiro, A. L. Org. Lett. 2000, 2, 2881-2884. (c) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058-9064. (d) Munoz, M. P.; Martin-Matute, B.; Fernandez-Rivas, C.; Cardenas, D. J.; Echavarren, A. M. Adv. Synth. Catal. 2001, 343, 338-342. (e) Alonso, D. A.; Najera, C.; Pacheco, M. C. Adv. Synth. Catal. 2002, 344, 172-183. (f) Morales-Morales, D.; Redon, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619-1620. (g) Albisson, D. A.; Bedford, R. B.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793-9796.
11. See for example: (a) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357-358. (b) Zim, D.; Gruber, A. S.; Ebeling, G.; Dupont, J.; Monteiro, A. L. Org. Lett. 2000, 2, 2881-2884. (c) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058-9064. (d) Munoz, M. P.; Martin-Matute, B.; Fernandez-Rivas, C.; Cardenas, D. J.; Echavarren, A. M. Adv. Synth. Catal. 2001, 343, 338-342. (e) Alonso, D. A.; Najera, C.; Pacheco, M. C. Adv. Synth. Catal. 2002, 344, 172-183. (f) Morales-Morales, D.; Redon, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619-1620. (g) Albisson, D. A.; Bedford, R. B.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793-9796.
12. Beletskaya, I. P.; Kashin, A. N.; Karlstedt, N. B.; Mitin, A. V.; Cheprakov, A. V.; Kazankov, G. M. J. Organomet. Chem. 2001, 622, 89-96.
13. Biffis, A.; Zecca, M.; Basato, M. Eur. J. Inorg. Chem. 2001, 1131-1133.
14. (a) Dupont, J.; Basso, N. R.; Meneghetti, M. R. Polyhedron 1996, 15, 2299-2302.
15. (b) Dupont, J.; Basso, N. R.; Meneghetti, M. R.; Konrath, R. A.; Burrow, R.; Horner, M. Organometallics 1997, 16, 2386-2391.
16. (c) Ebeling, G.; Meneghetti, M. R.; Rominger, F.; Dupont, J. Organometallics 2002, 21, 3221-3227.
17. Zanini, M. L.; Ebeling, G.; Livotto, P. R.; Marken. F.; Meneghetti, M. R.; Dupont, J. Polyhedron 2003, accepted for publication.
18. Gruber, A. S.; Pozebon, D.; Monteiro, A. L.; Dupont, J. Tetrahedron Lett. 2001, 42, 7345-7348.
19. (a) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000.
20. (b) Deshmukh, R. R.; Rajagopal, R.; Srinivasan, K. V. Chem. Commun. 2001, 1544-1545.
21. For a review about the use of molten salts in catalysis, see: Dupont, J. ; deSouza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692.
22. For a recent review of Pd-catalyzed coupling reactions of chloroarenes, see: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed, 2002, 41, 4176-4211.
23. Experiment was validated by determining the relative initial reaction rate of experiments performed separately (activated from deactivated bromoarenes).
24. Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1665-1673.
25. Weissman, H.; Milstein, D. Chem. Commun. 1999, 1901-1902.
26. Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287-1290.
27. For recent studies on the Heck reaction mechanism, see: (a) Amatore, C.; Carré, E.; Jutand, A.; Medjour, Y. Organometallics 2002, 21, 4540-4545. (b) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314-321.
28. For recent studies on the Heck reaction mechanism, see: (a) Amatore, C.; Carré, E.; Jutand, A.; Medjour, Y. Organometallics 2002, 21, 4540-4545. (b) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314-321.
29. 2 does not promote the Heck coupling at room temperature (see ref 9).
30. 2 does not promote the Heck coupling at room temperature (see ref 9).
31. Hg(0) poisoning was performed according to: Weddle, K. S.; Aiken, J. D.; Finke, R. G. J. Am. Chem. Soc. 1998, 120, 5653-5666.
32. After the submission of this manuscript, Gladysz reported the identification of Pd nanoparticles in Heck coupling promoted by palladacycles: Rocaboy, C.; Gladysz, J. A. New J. Chem. 2003, 27, 39-49.