Pd(N,N-dimethyl β-alaninate)2 as a high-turnover-number, phosphine-free catalyst for the suzuki reaction

Synthesis

Volumn , Issue 3, 2007, Pages 0393-0399

  Cui, Xin ^a   Qin, Tian ^a   Wang, Jia Rui ^a   Liu, Lei ^a   Guo, Qing Xiang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

High turnover number catalyst; Palladium; Phosphine free ligand; Suzuki reaction

Indexed keywords

ARYL BROMIDES; HIGH-TURNOVER-NUMBER CATALYSTS; PHOSPHINE; PHOSPHINE-FREE LIGANDS; SUZUKI REACTION;

BROMINE COMPOUNDS; CATALYSTS; LIGANDS; OLEFINS; SYNTHESIS (CHEMICAL);

PALLADIUM COMPOUNDS;

4 BROMOTOLUENE; ALKENE; BORON DERIVATIVE; BROMINE DERIVATIVE; IODINE DERIVATIVE; PALLADIUM COMPLEX; PALLADIUM(N,N DIMETHYL BETA ALANINATE); PHENYBORONIC ACID; PHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; SUZUKI REACTION; SYNTHESIS;

EID: 33947499291     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-965883     Document Type: Article

References (55)

1. Recent reviews: (a) Suzuki, A. Chem. Commun. 2005, 4759.
2. (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4442.
3. (c) Bellina, F.; Carpita, A.; Rossi, R. Synthesis 2004, 2419.
4. (d) Miura, M. Angew. Chem. Int. Ed. 2004, 43, 2201.
5. (e) Wang, Y.-F.; Deng, W.; Liu, L.; Guo, Q.-X. Chin. J. Org. Chem. 2005, 25, 8.
6. (f) Liang, Y.; Li, J.-H. Chin. J. Org. Chem. 2005, 25, 147.
7. (g) Shao, Z.-H.; Zhang, H.-B. Chin. J. Org. Chem. 2005, 25, 282.
8. (h) Han, X.-L.; Liu, G.-X.; Lu, X.-Y. Chin. J. Org. Chem. 2005, 25, 1182.
9. (a) Farina, V. Adv. Synth. Catal. 2004, 346, 1553.
10. (b) Phan, N. T. S.; Van Der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609.
11. 3, i.e. a catalyst that can lead to complete conversion of starting materials at a load of 0.1% mol, will be considered as a high-turnover-number catalyst.
12. (a) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804.
13. (b) Gstottmayr, C. W. K.; Bohm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. Angew. Chem. Int. Ed. 2002, 41, 1363.
14. (c) Navarro, O.; Kelly, R. A. III; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194.
15. (a) Tao, B.; Boykin, D. W. Tetrahedron Lett. 2002, 43, 4955.
16. (b) Wang, L.; Li, P.-H. Chin. J. Chem. 2006, 24, 770.
17. (a) Alonso, D. A.; Najera, C.; Pacheco, M. C. Org. Lett. 2000, 2, 1823.
18. (b) Botella, L.; Najera, C. Angew. Chem. Int. Ed. 2002, 41, 179.
19. (c) Najera, C.; Gil-Molto, J.; Karlstorm, S.; Falvello, L. R. Org. Lett. 2003, 5, 1451.
20. (a) Weissman, H.; Milstein, D. Chem. Commun. 1999, 1901.
21. (b) Bedford, R. B.; Cazin, C. S. Chem. Commun. 2001, 1540.
22. (c) Wu, K.-M.; Huang, C.-A.; Peng, K.-F.; Chen, C.-T. Tetrahedron 2005, 61, 9679.
23. (d) Lai, Y.-C.; Chen, H.-Y.; Hung, W.-C.; Lin, C.-C.; Hong, F.-E. Tetrahedron 2005, 61, 9484.
24. Grasa, G. A.; Hillier, A. C.; Nolan, S. P. Org. Lett. 2001, 3, 1077.
25. (a) Tao, B.; Boykin, D. W. Tetrahedron Lett. 2003, 44, 7993.
26. (b) Li, J.-H.; Liu, W.-J. Org. Lett. 2004, 6, 2809.
27. (c) Li, J.-H.; Liu, W.-J.; Xie, Y.-X. J. Org. Chem. 2005, 70, 5409.
28. (d) Li, J.-H.; Liang, Y.; Wang, D.-P.; Liu, W.-J.; Xie, Y.-X.; Yin, D.-L. J. Org. Chem. 2005, 70, 2832.
29. (e) Zhang, L.; Cui, Y.-C. Acta Chim. Sinica 2005, 63, 924.
30. (f) Yang, Y.-F.; Zeng, C.-X.; Luo, M.-F.; Li, Q.-L.; Huang, C.-B. Acta Chim. Sinica 2005, 63, 1469.
31. (g) Yi, H.; Liu, J. B.; Li, Q.; Tang, J. Chin. Chem. Lett. 2005, 16, 1173.
32. (h) Cui, Y.-C.; Zhao, X.-W.; Zhang, J.-W.; Zhang, L.; Liu, X.-M. Acta Chim. Sinica 2006, 64, 42.
33. (i) Xie, Y.-X.; Li, J.-H.; Yin, D.-L. Chin. J. Org. Chem. 2006, 26, 1155.
34. (j) Yang, Y.-F.; Zhuang, M.; Zeng, C.-X.; Huang, C.-B.; Luo, M.-F. Chin. J. Chem. 2006, 24, 1309.
35. Najera, C.; Gil-Molto, J.; Karlstrom, S. Adv. Synth. Catal. 2004, 346, 1798.
36. (a) Mino, T.; Shirae, Y.; Sakamoto, M.; Fujita, T. Synlett 2003, 882.
37. (b) Mino, T.; Shirae, Y.; Sakamoto, M.; Fujita, T. J. Org. Chem. 2005, 70, 2191.
38. Mukherjee, A.; Sarkar, A. Tetrahedron Lett. 2005, 46, 15.
39. (a) Liu, L.; Zhang, Y.; Wang, Y. J. Org. Chem. 2005, 70, 6122.
40. (b) Xin, B.; Zhang, Y.; Cheng, K. J. Org. Chem. 2006, 71, 5725.
41. Deng, W.; Liu, L.; Zhang, C.; Liu, M.; Guo, Q.-X. Tetrahedron Lett. 2005, 46, 7295.
42. Cui, X.; Li, Z.; Tao, C.-Z.; Xu, Y.; Li, J.; Liu, L.; Guo, Q.-X. Org. Lett. 2006, 8, 2467.
43. For some recent examples, see: (a) Gossage, R. A.; Jenkins, H. A.; Yadav, P. N. Tetrahedron Lett. 2004, 45, 7689.
44. (b) Dai, M.; Liang, B.; Wang, C.; You, Z.; Xiang, J.; Dong, G.; Chen, J.; Yang, Z. Adv. Synth. Catal. 2004, 346, 1669.
45. (c) Lee, S. J. Organomet. Chem. 2006, 691, 1347.
46. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
47. (b) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127.
48. Xu, N.; Wang, Q.-R.; Tao, F.-G. Chin. J. Org. Chem. 2005, 25, 458.
49. Zou, Y.; Wang, Q.-R.; Tao, F.-G.; Ding, Z.-B. Chin. J. Chem. 2004, 22, 215.
50. Li, J.-F.; Bai, G.; Lin, P.-H.; Tian, M.-L.; Dong, C.; Li, D.-X. Chem. Res. Chin. Univ. 2004, 20, 216.
51. Enokido, T.; Fugami, K.; Endo, M.; Kameyama, M.; Kosugi, M. Adv. Synth. Catal. 2004, 346, 1685.
52. Denmark, S. E.; Ober, M. H. Org. Lett. 2003, 5, 1357.
53. Dai, M.-J.; Liang, B.; Wang, C.-H.; Chen, J.-H.; Yang, Z. Org. Lett. 2003, 6, 221.
54. Riggleman, S.; DeShong, P. J. Org. Chem. 2003, 68, 8106.
55. Arvela, R. K.; Leadbeater, N. E. Org. Lett. 2005, 7, 2101.