SnCl2/Cu-mediated carbonyl allylation reaction in water: Scope, selectivity and mechanism

Chinese Journal of Chemistry

Volumn 22, Issue 5, 2004, Pages 450-454

  Tan, Xiang Hui ^a   Hou, Yong Quan ^a   Liu, Lei ^a   Guo, Qing Xiang ^a  

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

Author keywords

Aqueous media; Barbier reaction; Carbonyl allylation; Copper; Green chemistry; Tin dichloride

Indexed keywords

ALCOHOL DERIVATIVE; CARBONYL DERIVATIVE; COPPER DERIVATIVE; HYDROXYL GROUP; NITRO DERIVATIVE; TIN CHLORIDE; WATER;

ALLYLATION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 3042812977     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.20040220512     Document Type: Article

References (36)

1. (a) Li, C. J. Chem. Rev. 1993, 93, 2023.
2. (b) Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741.
3. (c) Li, C. J. Tetrahedron 1996, 52, 5643.
4. (d) Zhu, Z.-Q.; Zeng, J.-Q. Chin. J. Org. Chem. 2001, 21, 1095 (in Chinese).
5. (e) Lindstroem, U. M. Chem. Rev. 2002, 102, 2751.
6. (a) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181.
7. (b) Cintas, P. Synlett 1995, 1087.
8. (c) Chan, Y. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228.
9. (d) Loh, T. P.; Zhou, J. R.; Yin, Z. Org. Lett. 1999, 1, 1855.
10. (f) Yuan, Y.-F.; Cao, Z.; Hu, A.-G.; Wang, J.-T. Chin. J. Org. Chem. 2000, 20, 269 (in Chinese).
11. (g) Hilt, G.; Smolko, K. I.; Waloch, C. Tetrahedron Lett. 2002, 43, 1437
12. Li, L. H.; Chan, T. H. Tetrahedron Lett. 2000, 41, 5009.
13. (a) Wada, M.; Ohki, H.; Akiba, K. Y. Bull. Chem. Soc. Jpn. 1990, 63, 2751.
14. (b) Ren, P.-D.; Pan, S.-F.; Dong, T.-W.; Wu, S.-H. Chin. J. Chem. 1996, 14, 462.
15. (a) Zhou, J. Y.; Jia, Y.; Sun, G. F.; Wu, S. H. Synth. Commun. 1997, 27, 1899.
16. (b) Zhou, J.-Y.; Sun, G.-F.; Zhang, M.-F.; Jia, Y.; Wu, S.-H. Chin. J. Chem. 1997, 15, 361.
17. Li, C. J.; Meng, Y.; Yi, X. H.; Ma, J. H.; Chan, T. H. J. Org. Chem. 1998, 63, 7498.
18. Zhang, W. C.; Li, C. J. J. Org. Chem. 1999, 64, 3230.
19. (a) Petrier C.; Luche, J. L. J. Org. Chem. 1999, 64, 3230.
20. (b) Deng, D.; Lu, Z. Chin. Chem. Lett. 1994, 5, 173.
21. (c) Deng, D.-L.; Lu, Z.-H.; Wu, K. Chin. J. Org. Chem. 1996, 16, 462 (in Chinese).
22. (d) Marton, D.; Stivanello, D.; Tagliavini, G. J. Org. Chem. 1996, 61, 2731.
23. (e) Yi, X. H.; Haberman, J. X.; Li, C. J. Synth. Commun. 1998, 28, 2999.
24. (a) Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 1527.
25. (b) Wu, S.; Zhu, T. Acta Chim. Sinica 1987, 45, 1135 (in Chinese).
26. (c) Wu, S. H.; Huang, B. Z.; Zhu, T. M.; Yiao, D. Z.; Chu, Y. L. Acta Chim. Sinica 1990, 48, 372 (in Chinese).
27. (d) Chan, T. H.; Yang, Y.; Li, C. J. J. Org. Chem. 1999, 64, 4452.
28. (e) Zou, C.-L.; Zha, Z.-G.; Wang, Z.-Y.; Wu, J.-H.; Zhang, J.-H. Chin. J. Chem. 2002, 20, 718.
29. (f) Zha, Z.-G.; Xie, Z.; Zhou, C.-L.; Wang, Z.-Y.; Wang, Y.-S. Chin. J. Chem. 2002, 20, 1477.
30. Wang, Z.-Y.; Yuan, S.-Z.; Zha, Z.-G.; Zhang, Z.-D. Chin. J. Chem. 2003, 21, 1231.
31. Takahara, J. P.; Masuyama, Y.; Kurusu, Y. J. Am. Chem. Soc. 1992, 114, 2577.
32. Kundu, A.; Prabhakar, S.; Vairamini, M.; Roy, S. Organometallics 1997, 16, 4796.
33. Preliminary communication: Tan, X.-H.; Shen, B.; Liu, L.; Quo, Q.-X. Tetrahedron Lett. 2002, 43, 9373.
34. For review, see: (a) Li, C. J.; Chan, T.-H. Tetrahedron 1999, 55, 1149.
35. (b) Li, C. J. Tetrahedron 1996, 52, 5643.
36. Tan, K.-T.; Chng, S.-S.; Cheng, H.-S.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 2958.