N,N-dimethyl-β-alanine as an inexpensive and efficient ligand for palladium-catalyzed Heck reaction

Organic Letters

Volumn 8, Issue 12, 2006, Pages 2467-2470

  Cui, Xin ^a   Li, Zhe ^a   Tao, Chuan Zhou ^a   Xu, Yu ^a   Li, Juan ^a   Liu, Lei ^a   Guo, Qing Xiang ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

2,2 DIMETHYL BETA ALANINE; 2,2-DIMETHYL-BETA-ALANINE; BETA ALANINE; DRUG DERIVATIVE; LIGAND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ECONOMICS;

BETA-ALANINE; CATALYSIS; LIGANDS; MOLECULAR STRUCTURE; PALLADIUM;

EID: 33745521123     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060585n     Document Type: Article

References (43)

1. (a) De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1995, 33, 2379.
2. (b) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
3. (c) Donnay, A. B.; Overman, L. E. Chem. Reu. 2003, 103, 2945.
4. Farina, V. Adv. Synth. Catal. 2004, 346, 1553.
5. 3 turnover number, i.e., a catalyst that can lead to complete conversion of starting materials at a load of 0.1% mol, will be considered as an HTC.
6. Recent reviews: (a) Bedford, R. B. Chem. Commun. 2003, 1787.
7. (b) Herrmann, W. A.; Ofele, K.; von Preysing, D.; Schneider, S. K. J. Organomet. Chem. 2003, 687, 229.
8. (c) De Vries, J. G. Dalton Trans. 2006, 421.
9. Recent reviews: (a) Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69.
10. (b) Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2239.
11. (a) Dai, M. J.; Liang, B.; Wang, C. H.; You, Z. J.; Xiang, J.; Dong, G. B.; Chen, J. H.; Yang, Z. Adv. Synth. Catal. 2004, 346, 1669.
12. (b) Yang, D.; Chen, Y. C.; Zhu N. Y. Org. Lett. 2004, 6, 1577.
13. (c) Chen, W.; Li, R.; Han, B.; Li, B. J.; Chen, Y. C.; Wu, Y.; Ding L. S.; Yang, D. Eur. J. Org. Chem. 2006, 1177.
14. (a) Grasa, G. A.; Singh, R.; Stevens, E. D.; Nolan, S. P. J. Organomet. Chem. 2003, 687, 269.
15. (b) Arellano, C. G.; Corma, A.; Iglesias, M.; Sanchez, F.; Adv. Synth. Catal. 2004, 346, 1758.
16. (c) Hardy, J. E.; Hubert, S.; Macquarrie, D. J.; Wilson, A. J. Green Chem. 2004, 6, 53.
17. (d) Domin, D.; Benito-Garagorri, D.; Mereiter, K.; Frohlich, J.; Kirchner, K. Organometallics 2005, 24, 3957.
18. (a) Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101.
19. (b) Buchmeiser, M. R.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39.
20. (c) Kawano, T.; Shinomaru, T.; Ueda, I. Org. Lett. 2002, 4, 2545.
21. (d) Najera, C.; Gil-Moito, J.; Karlstrum, S.; Falvello, L. R. Org. Lett. 2003, 5, 1451.
22. Cabri, W.; Candiani, I.; Bedeschi, A. J. Org. Chem. 1993, 58, 7421.
23. Mino, T.; Shirae, Y.; Sakamoto, M.; Fujita, T. J. Org. Chem. 2005, 70, 2191.
24. Li, S. H.; Xie, H. B.; Zhang, S. B.; Lin, Y. J.; Xu, J. N.; Cao, J. G. Synlett. 2005, 12, 1885.
25. Iyer, S.; Kulkarni, G. M.; Ramesh, C. Tetrahedron 2004, 60, 2163.
26. Gossage, P. A.; Jenkins, H. A.; Yadav, P. N. Tetrahedron Lett. 2004, 45, 7689.
27. Kovala-Demertzi, D.; Yadav, P. N.; Demertzis, M. A.; Jasiski, J. P.; Andreadaki, F. J.; Kostas, I. D. Tetrahedron Lett. 2004, 45, 2923.
28. Gupta, A. K.; Song, C. H.; Oh, C. H. Tetrahedron Lett. 2004, 45, 4113.
29. (a) Done, M. C.; Ruther, T.; Cavell, K. J.; Kilner, M.; Peacock, E. J.; Braussaud, N.; Skelton, B. W.; White, A. J. Organomet. Chem. 2000, 607, 78.
30. (b) Park, S. B.; Alper, H. Org. Lett. 2003, 5, 3209.
31. (c) Xiao, J. C.; Twamley, B.; Shreeve, J. M. Org. Lett. 2004, 6, 3845.
32. Reetz, M. T.; Westermann, E.; Lohmer, R. Lohmer, G. Tetrahedron Lett. 1998, 39, 8449.
33. (a) Deng, W.; Liu, L.; Zhang, C.; Liu, M.; Guo, Q.-X. Tetrahedron Lett. 2005, 46, 7295.
34. (b) Deng, W.; Zou, Y.; Wang, Y.-F.; Liu, L.; Guo, Q.-X. Synlett 2004, 1254.
35. (c) Deng, W.; Wang, Y.-F.; Zou, Y.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2004, 45, 2311.
36. Compound 1 was purchased. Compound 2 was prepared by methylation of β-alanine. Compound 3 was prepared by hydrolysis and subsequent methylation of N-methyl-2-pyrrolidone. They were all used as their hydrochloride salts.
37. (a) Lin, B.-L.; Liu, L.; Fu, Y.; Luo, S.-W.; Chen, Q.; Guo, Q.-X. Organometallics 2004, 23, 2114.
38. (b) Kozuch, S.; Amatore, C.; Jutand, A.; Shaik, S. Organometallics 2005, 24, 2319.
39. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
40. Li, Z.; Liu, L.; Fu, Y.; Guo, Q.-X. THEOCHEM 2005, 757, 69.
41. Amatore and Jutand have also shown that coordination by carboxylates can enhance the activity of Pd catalysts. See: Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
42. "Ligandless" Pd catalysts could accomplish some Heck reactions, if some additives (e.g., TBAB) are used to stablize Pd(0). See: (a) Yao, Q.; Kinney, E. P.; Yang, Z. J. Org. Chem. 2003, 68, 7528.
43. (b) Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2005, 61, 11771.