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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 23
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Original Articles

Et3B-mediated palladium-catalyzed direct allylic substitution reactions of Morita–Baylis–Hillman alcohols with aromatic amines

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Pages 1916-1923 | Received 30 Jul 2016, Published online: 07 Oct 2016

References

  • (a) Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689; (b) Tsuji J. Transition Metal Reagents and Catalysts; Wiley: New York, 2000; (c) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
  • (a) Tao, Y.; Wang, B.; Wang, B.; Qu, L.; Qu J. Org. Lett. 2010, 12, 2726; (b) Ghosh, R.; Sarkar, A. J. Org. Chem. 2011, 76, 8508; (c) Sawadjoon, S.; Sjçberg, P. J. R.; Orthaber, A.; Matsson, O.; Samec, J. S. M. Chem. Eur. J. 2014, 20, 1520; (d) Gumrukcu, Y.; Bruin, B. d.; Reek, J. N. H. Catalysts 2015, 5, 349; (e) Kayaki, Y.; Koda, T.; Ikariya, T. J. Org. Chem. 2004, 69, 2595; (f) Bass, J. D.; Solovyov, A.; Pascall, A. J.; Katz, A. J. Am. Chem. Soc. 2006, 128, 14306; (g) Kinoshita, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 4085; (h) Utsunomiya, M.; Miyamoto, Y.; Ipposhi, J.; Ohshima, T.; Mashima, K. Org. Lett. 2007, 9, 3371; (i) Butt, N. A.; Zhang, W. Chem. Soc. Rev. 2015, 44, 7929.
  • Ozawa, F.; Okamoto, H.; Kawagishi, S.; Yamamoto, S.; Minami, T.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124, 10968.
  • Muzart, J. Eur. J. Org. Chem. 2007, 3077.
  • (a) Zhuang, M.; Du, H.; Org. Biomol. Chem. 2014, 12, 4590; (b) Kang, K.; Kim, J.; Lee, A.; Kim, W. Y.; Kim, H. Org. Lett. 2016, 18, 616.
  • (a) Hsu, Y.-C.; Gan, K.-H.; Yang, S.-C. Chem. Pharm. Bull. 2005, 53, 1266; (b) Tamaru, Y. Eur. J. Org. Chem. 2005, 2647.
  • Kimura, M.; Futamata, M.; Shibata, K.; Tamaru, Y. J. Chem. Soc., Chem. Commun. 2003, 234.
  • Muzart, J. Tetrahedron 2005, 61, 4179.
  • For recent advances in the Baylis–Hillman reaction, see (a) Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627; (b) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811; (c) Gowrisankar, S.; Lee, H. S.; Kim, S. H.; Lee, K. Y.; Kim, J. N. Tetrahedron 2009, 65, 8769; (d) Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447.
  • (a) Rajesh, S.; Banerji, B.; Iqbal, J. J. Org. Chem. 2002, 67, 7852; (b) Fukuyama, T.; Yamamoto, E.; Tamura, S.; Fukuda, T.; Matsumoto, T.; Akimoto, Y.; Hamada, Y. Org. Lett. 2007, 9, 927; (c) Cao, H.; Vieira, T. O.; Alper, H. Org. Lett. 2011, 13, 11.
  • Wang, Y.; Liu, L.; Wang, D.; Chen, Y.-J. Org. Biomol. Chem. 2012, 10, 6908.
  • Liu, Y.-L.; Liu, L.; Wang, D.; Chen, Y.-J. Tetrahedron 2009, 65, 3473.
  • Mhasni, O.; Rezgui, F. Tetrahedron Lett. 2010, 51, 586.
  • Erray, I.; Oble, J.; Poli, G.; Rezgui, F. J. Sulfur. Chem 2014, 35, 128.
  • Elleuch, H.; Ayadi, M.; Bouajila, J.; Rezgui, F. J. Org. Chem. 2016, 81, 1757.
  • Rezgui, F.; El Gaied, M. M. Tetrahedron Lett. 1998, 39, 5965.
  • Gatri, R.; El Gaied, M. M. Tetrahedron Lett. 2002, 43, 7835.
  • (a) Tamura, R.; Katayamaa, H.; Watabea, K.; Suzuki, H. Tetrahedron 1990, 46, 7557; (b) Okamoto, S.; Kobayashi, Y.; Kato, H.; Takashi, H.; Jiro Tsuji, T.; Sato, F. J. Org. Chem. 1988, 53, 5590 (c) K. Y. Lee, H. S. Lee, J. N. Kim Bull. Korean Chem. Soc. 2008, 29, 1099.
  • For evidence of the formation of Pd(0) species from Pd(OAc)2 and PPh3, see (a) Amatore, C.; Jutand, A.; M’Barki, M. A. Organometallics 1992, 11, 3009; (b) Fors, B. P.; Krattiger, P.; Strieter, E.; Buchwald, S. L. Org. Lett. 2008, 10, 3505.
  • Poli, G.; Prestat, G.; Liron, F.; Kammerer-Pentier, C. Top. Organomet. Chem. 2012, 38, 1–64; Selectivity in Palladium-Catalyzed Allylic Substitution; Springer-Verlag: Berlin, 2011.
  • Luo, S.; Wang, P. G.; Cheng, J.-P. J. Org. Chem. 2004, 69, 555.
  • Villiéras, J.; Rambaud, M. Org. Synth. 1993, 8, 265.
  • Amri, H.; El Gaied, M. M.; Ben Ayed, T.; Villiéras, J. Tetrahedron Lett. 1992, 33, 6159.

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