Simple and Clean Synthesis: Tin-mediated Allylation of Carbonyl Compounds in Water
Cun-Liu Zhou
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorZheng-Gen Zha
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorZhi-Yong Wang
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorJi-Hui Wu
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorJia-Hai Zhang
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorCun-Liu Zhou
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorZheng-Gen Zha
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorZhi-Yong Wang
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorJi-Hui Wu
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorJia-Hai Zhang
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorAbstract
Tin-mediated allylation of aldehydes or ketones in distilled water gives rise to the corresponding homoallyl alcohols in high yield without assistance such as heat, supersonic and acidic media.
References
- 1(a) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media, John Wiley & Sons Inc., New York, 1993. (b) Li, C. J. Chem. Rev. 1993, 93, 2023. (c) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181. (d) Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. (e) Li, C. J. Tetrahedron 1996, 52, 5643. (f) Chan, T. H.; Isaac, B. M. Pure Appl. Chem. 1996, 68, 919.
- 2(a) Einhom, C.; Luche, J. L. Organomet. Chem. 1987, 322, 177. (b) Petrier, C.; Einhom, J.; Luche, J. L. Tetrahedron Lett. 1985, 26, 1449. (c) Nokami, J.; Wakababayashi, S.; Okawara, R. Chem. Lett. 1984, 869. (d) Wu, S. H.; Huang, B. Z.; Zhu, T. M.; Yiao, D. Z.; Chu, Y. L. Acta Chim. Sinica 1990, 48, 372 (in Chinese). (e) Green Chemistry; Frontiers in Benign Chemical Synthesis and Processing, Eds.; P. Anastas; T. C. Williamson Oxford University Press, New York, 1988. (f) Li, C. J.; Meng, Y.; Yi, X. H. J. Org. Chem. 1997, 62, 8632.
- 3(a) Li, C. J.; Meng, Y.; Yi, X. H. J. Org. Chem. 1998, 63, 7498. (b) Wada, M.; Fukuma, T. Tetrahedron Lett. 1997, 38, 8045.
- 4 Li, L. H.; Chan, T. H. Org. Lett. 2000, 2, 1129.
- 5(a) Wang, Z. Y.; Zha, Z. G. Org. Lett. 2002, 4, 1683. (b) Chan, T. H.; Yang, Y.; Li, C. J. J. Org. Chem. 1999, 64, 4452. (c) Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071. (d) Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747.
- 6(a) Chan, T. H.; Yang, Y. Tetrahedron Lett. 1999, 40, 3836. (b) Zhang, W. C.; Li, C. J. J. Org. Chem. 1999, 64, 3230. (c) Li, C. J.; Zhang, W. C. J. Am. Chem. Soc. 1998, 120, 9102.
- 7(a) Yi, X. H.; Haberman, J. X.; Li, C. J. Synth. Commun. 1998, 28, 2999. (b) Loh, T. P.; Xu, J.; Loh, T. Tetrahedron Lett. 1999, 40, 2431.
- 8 Akiyama, T.; Iwai, J. Tetrahedron Lett. 1997, 38, 853.
- 9(a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Uneyama, K.; Kamaki, N.; Moriya, A.; Torii, S. J. Org. Chem. 1985, 50, 5396. (c) Mandai, T.; Nokami, J.; Yano, T.; Yoshinoga, Y.; Otera, J. J. Org. Chem. 1984, 49, 172. (d) Loh, T. P.; Xu, J.; Hu, Q. Y. Tetrahedron: Asymmetry 2000, 11, 1565.
- 10(a)
Moody, C. J.;
Pitts, M. P.
Synlett
1998,
1028.
10.1055/s-1998-1837 Google Scholar(b) Moody, C. J.; Pitts, M. P. Synlett 1998, 1029.10.1055/s-1998-1836 Google Scholar
- 11 Smith, P. J. Toxicological Data on Organotin Compounds, International Tin research Inst., London, 1978.
- 12 IR (Perkin-Elmer, 2000FTIR), NMR (Bruker DMX500) and MS-GC (HP 5890(II)/HP5972, EI) spectral data are as follows; 1-Phenyl-3-buten-1-ol (3a)13 1H NMR (CDCl3, 500 MHz) δ: 2.40 (t, J = 7.13, 6.59 Hz, 2H), 2.91–2.98 (br, 1H), 4.57 (t, J = 6.59 Hz, 1H), 5.02–5.04 (m, 1H), 5.03–5.06 (m, 1H), 5.66–5.74 (m, 1H), 7.29–7.70 (m, 5H); 13C NMR (CDCl3, 125.7 MHz) δ: 43.64,73.40, 117.94, 125.92, 127.41, 128.30, 134.55.
- 13 Li, C. J.; Meng, Y.; X., H. J. J. Org. Chem. 1998, 63, 7498.
- 14 Lysenko, F. U. Izv. Vyssh. Ucheb. Zaved., Khim, Khim, Tekhnol. 1971, 14(2), 242 (in Russia).
- 15 Tanaka, K.; Kishigami, S.; Toda, F. J. Org. Chem. 1991, 56, 4333.
- 16 Chan, T. H.; Yang, Y.; Li, C. J. J. Org. Chem. 1991, 64, 4452.