Sterically bulky thioureas as air- and moisture-stable ligands for pd-catalyzed heck reactions of aryl halides

Organic Letters

Volumn 6, Issue 10, 2004, Pages 1577-1580

  Yang, Dan ^a   Chen, Ying Chun ^a   Zhu, Nian Yong ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID METHYL ESTER; ALKENE DERIVATIVE; BROMINE DERIVATIVE; CHLORINE DERIVATIVE; HALIDE; IODINE DERIVATIVE; PALLADIUM; THIOUREA DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; COMPLEX FORMATION; HECK REACTION;

EID: 2542543701     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049697+     Document Type: Article

References (49)

1. (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
2. (b) De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. 1994, 33, 2379.
3. (c) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
4. (d) Negishi, E.; Coperet, C.; Ma, S.; Liou, S.; Liu, F. Chem. Rev. 1996, 96, 365.
5. (e) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427.
6. (f) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
7. (g) Whitcombe, N. J.; Kuok Hii, K.; Gibson, S. E. Tetrahedron 2001, 57, 7449.
8. (h) Dounay, A. B.; Overman, L. E. Chem Rev. 2003, 103, 2945.
9. (a) Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10.
10. (b) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989.
11. (c) Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123.
12. (d) Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2677.
13. (e) Ehrentraut, A.; Zapf, A.; Beller, M. Synlett 2000, 1589.
14. (a) Ben-David, Y.; Portnoy, M.; Gozin, M.; Milstein, D. Organometallics 1992, 11, 1995.
15. (b) Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1655.
16. (c) Portnoy, M.; Ben-David, Y.; Milstein, D. Organometallics 1993, 12, 4734.
17. (d) Portnoy, M.; Ben-Dvid, Y.; Rousso, I.; Milstein, D. Organometallics 1994, 13, 3465.
18. (e) Shaw, B. L.; Perera, S. D. Chem. Commun. 1998, 1863.
19. For recent reviews on palladacycles for Heck reactions, see: (a) Dupont, J.; Pfeffer, M.; Spencer, J. Eur. J. Inorg. Chem. 2001, 1917. (b) Benford, R. B. Chem. Commun. 2003, 1787.
20. For recent reviews on palladacycles for Heck reactions, see: (a) Dupont, J.; Pfeffer, M.; Spencer, J. Eur. J. Inorg. Chem. 2001, 1917. (b) Benford, R. B. Chem. Commun. 2003, 1787.
21. For the use of tetraphenylphosphonium salts in Heck reactions, see: Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. 1998, 37, 481.
22. For phosphorus-free palladacycles as catalysts, see ref 4.
23. For recent reviews on N-heterocyclic carbene-palladium catalysts, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (b) Yong, B. S.; Nolan, S. P. Chemtracts: Org. Chem. 2003, 205.
24. For recent reviews on N-heterocyclic carbene-palladium catalysts, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (b) Yong, B. S.; Nolan, S. P. Chemtracts: Org. Chem. 2003, 205.
25. For recent reports on Heck reactions using catalysts that are air- and moisture-stable, see: (a) Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101. (b) Silberg, J.; Schareina, T.; Kempe, R.; Wurst, K.; Buchmeiser, M. R. J. Organomet. Chem. 2001, 622, 6. (c) Masllorens, J.; Moreno-Manas, M.; Pla-Quintana, A.; Roglans, A. Org. Lett. 2003, 5, 1559.
26. For recent reports on Heck reactions using catalysts that are air- and moisture-stable, see: (a) Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101. (b) Silberg, J.; Schareina, T.; Kempe, R.; Wurst, K.; Buchmeiser, M. R. J. Organomet. Chem. 2001, 622, 6. (c) Masllorens, J.; Moreno-Manas, M.; Pla-Quintana, A.; Roglans, A. Org. Lett. 2003, 5, 1559.
27. For recent reports on Heck reactions using catalysts that are air- and moisture-stable, see: (a) Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101. (b) Silberg, J.; Schareina, T.; Kempe, R.; Wurst, K.; Buchmeiser, M. R. J. Organomet. Chem. 2001, 622, 6. (c) Masllorens, J.; Moreno-Manas, M.; Pla-Quintana, A.; Roglans, A. Org. Lett. 2003, 5, 1559.
28. (a) Touchard, F.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1997, 8, 3319.
29. (b) Touchard, F.; Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron Lett. 1997, 38, 2275.
30. (c) Touchard, F.; Bernard, M.; Fache, F.; Delbecq, F.; Guiral, V.; Sautet, P.; Lemaire, M. J. Organomet. Chem. 1998, 567, 133.
31. (d) Tommasino, M. L.; Casalta, M.; Breuzard, J. A. J.; Lemaire, M. Tetrahedron: Asymmetry 2000, 11, 4835.
32. (e) Breuzard, J. A. J.; Tommasino, M. L.; Touchard, F.; Lemaire, M.; Bonnet, M. C. J. Mol. Catal. A: Chem. 2000, 156, 223.
33. (f) Touchard, F.; Bernard, M.; Fache, F.; Lemaire, M. J. Mol. Catal. A: Chem. 1999, 140, 1.
34. (a) De Munno, G.; Gabriele, B.; Salerno, G. Inorg. Chim. Acta 1995, 234, 181.
35. (b) Gabriele, B.; Salerno, G.; Costa, M.; Chiusoli, G. P. J. Organomet. Chem. 1995, 503, 21.
36. (c) Zhang, T. Y.; Allen, M. J. Tetrahedron Lett. 1999, 40, 5813.
37. (d) Nan, Y.; Miao, H.; Yang, Z. Org. Lett. 2000, 2, 297.
38. (e) Miao, H.; Yang, Z. Org. Lett. 2000, 2, 1765.
39. (f) Hu, Y.; Yang, Z. Org. Lett. 2001, 3, 1387.
40. Dai, M.; Liang, B.; Wang, C.; Chen, J.; Yang, Z. Org. Lett. 2004, 6, 221.
41. For the synthesis of the thiourea ligands, see Supporting Information.
42. Gurtler, C.; Buchwald, S. L. Chem. Eur. J. 1999, 5, 3107 and references therein.
43. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
44. Almost no reaction occurred at 100°C using ArBr as substrates.
45. Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031.
46. For recent reviews on the use of ionic liquids as solvents, see: (a) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A: Chem. 2002, 182-183, 419. (b) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. (c) Davis, J. H., Jr.; Fox, P. A. Chem. Commun. 2003, 1209.
47. For recent reviews on the use of ionic liquids as solvents, see: (a) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A: Chem. 2002, 182-183, 419. (b) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. (c) Davis, J. H., Jr.; Fox, P. A. Chem. Commun. 2003, 1209.
48. For recent reviews on the use of ionic liquids as solvents, see: (a) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A: Chem. 2002, 182-183, 419. (b) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. (c) Davis, J. H., Jr.; Fox, P. A. Chem. Commun. 2003, 1209.
49. 2 and thiourea 1g, both the yield and reaction rate were quite similar to those obtained when using a 1:4 ratio. Generally, however, almost no palladium black was formed when using Pd-thiourea in a 1:4 ratio, whereas trace amounts of Pd black could be observed when using the 1:2 ratio, especially after heating for an extended period of time.