Tetramethylguanidine as an inexpensive and efficient ligand for the palladium-catalyzed Heck reaction

Synlett

Volumn , Issue 12, 2005, Pages 1885-1888

  Li, Shenghai ^b   Xie, Haibo ^a   Zhang, Suobo ^a   Lin, Yingjie ^b   Xu, Jianing ^b   Cao, Jungang ^b  

^a CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

^b JUIN UNIVERSITY   (China)

Author keywords

Aryl halides; Heck reaction; Ligand; Palladium; Tetramethylguanidine

Indexed keywords

ACRYLIC ACID BUTYL ESTER; ALKENE; ARYL HALOGENIDE; BROMOBENZENE; GUANIDINE DERIVATIVE; IODOBENZENE; LIGAND; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; STYRENE; TETRAMETHYLGUANIDINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; HECK REACTION;

EID: 23644462060     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871581     Document Type: Article

References (43)

1. Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
2. Selected leading reviews and monographs on the Heck reaction: (a) Heck, R. F. In Comprehensive Organic Synthesis, Vol 4; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991, Chap. 4.3.
3. (b) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427.
4. (c) Casey, M.; Lawless, J.; Shirran, C. Polyhedron 2000, 19, 517.
5. (d) Beletskaya, I. P.; Cheprokov, A. V. Chem. Rev. 2000, 100, 3009.
6. (a) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989.
7. (b) Bohm, V. P. W.; Herrmann, W. A. Chem.-Eur. J. 2000, 6, 1017.
8. (c) Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123.
9. (d) Ehrentraut, A.; Zapf, A.; Beller, M. Synlett 2000, 1589.
10. (a) Ohff, M.; Ohff, A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687.
11. (b) Gibson, S.; Foster, D. F.; Eastam, G. R.; Tooze, R. P.; Cole-Hamilton, D. J. Chem. Commun. 2001, 779.
12. (c) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem. Int. Ed. 1995, 34, 1844.
13. (d) Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361.
14. (e) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379.
15. (f) Bedford, R. B.; Welch, S. L. Chem. Commun. 2001, 129.
16. (g) Morales-Morales, D.; Redón, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619.
17. (a) Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287.
18. (b) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058.
19. (c) Yang, D.; Chen, Y.-C.; Zhu, N.-Y. Org. Lett. 2004, 6, 1577.
20. Yao, Q.; Kinney, E. P.; Zheng, C. Org. Lett. 2004, 6, 2997.
21. (a) Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993.
22. (b) Tsai, F.-Y.; Wu, C.-L.; Mou, C.-Y.; Chao, M.-C.; Lin, H.-P.; Liu, S.-T. Tetrahedron Lett. 2004, 45, 7503.
23. (c) Alonso, D. A.; Nájera, C.; Pacheco, M. C. Adv. Synth. Catal. 2002, 344, 172.
24. (d) Gai, X.; Grigg, R.; Ramzan, M. L.; Sridharan, V.; Collard, S.; Muir, J. E. Chem. Commun. 2000, 2053.
25. (e) Alonso, D. A.; Najera, C.; Pacheco, M. C. Org. Lett. 2000, 2, 1823.
26. (f) Beletskaya, I. P.; Kashin, A. N.; Karlstedt, N. B.; Mitin, A. V.; Cheprakov, A. V.; Kazankov, G. M. J. Organomet. Chem. 2001, 622, 89.
27. (g) Muñoz, M. P.; Martín-Matute, B.; Fernández-Rivas, C.; Cárdenas, D. J.; Echavarren, A. M. Adv. Synth. Catal 2001, 343, 338.
28. (h) Consenti, C. S.; Zanini, M. L.; Leal, S.; Ebeling, G.; Dupont, J. Org. Lett. 2003, 5, 983.
29. (i) Gürtler, C.; Buchwald, S. L. Chem.-Eur. J. 1999, 5, 3107.
30. (j) Iyer, S.; Kulkarni, G. M.; Ramesh, C. Tetrahedron 2004, 60, 2163.
31. (k) Kawano, T.; Shinomaru, T.; Ueda, I. Org. Lett. 2002, 4, 2545.
32. (l) Park, S. B.; Alper, H. Org. Lett. 2003, 5, 3209.
33. (m) Najera, C.; Gil-Molto, J.; Karlstrom, S.; Falvello, L. R. Org. Lett. 2003, 5, 1451.
34. (a) Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290.
35. (b) Nolan, S. P.; Lee, H. M.; Yang, C. Org. Lett. 2001, 3, 1511.
36. (c) Peris, E.; Loch, J. A.; Mata, J.; Crabtree, R. H. Chem. Commun. 2001, 201.
37. (a) Simoni, D.; Invidiata, F. P.; Manferdini, M.; Lampronti, I.; Rondanin, R.; Roberti, M.; Pollini, G. P. Tetrahedron Lett. 1998, 39, 7615.
38. (b) Leadbeater, N. E.; van der Pol, C. J. Chem. Soc., Perkin Trans. 1 2001, 2831.
39. Longhi, R.; Drago, R. S. Inorg. Chem. 1965, 4, 11.
40. (a) Jeffery, T.; David, M. Tetrahedron Lett. 1998, 39, 5751.
41. (b) Jeffery, T. Tetrahedron Lett. 2000, 41, 8445.
42. 3, R1 = 0.0309, wR = 0.0894.
43. 1H NMR and GC.