Chinese Journal of Organic Chemistry >
Nucleophilic Substitution Reactions at Vinylic Carbons
Received date: 2014-06-27
Revised date: 2014-07-17
Online published: 2014-08-11
The recently research progress in the nucleophilic substitution reactions at the sp2-carbons, mainly at the vinylic carbons is reviewed. The theoretical studies on the nucleophilic substitution reactions at the vinylic carbons, and their applications in organic synthesis, especially in the synthesis of heterocycle compounds, are illustrated. And, researches and applications of the nucleophilic substitution reactions at other unsaturated atoms like sp2 nitrogens are also discussed.
Shen Shusu . Nucleophilic Substitution Reactions at Vinylic Carbons[J]. Chinese Journal of Organic Chemistry, 2014 , 34(12) : 2448 -2455 . DOI: 10.6023/cjoc201406046
[1] (a) Smith, M.; March, J. March's Advanced Organic Chemistry, 6th ed., Wiley-Interscience, New York, 2007, p. 425. (b) Hartshorn, S. R. Aliphatic Nucleophilic Substitution, Cambridge University Press, London, 1973. (c) Katritzky, A. R.; Brycki, B. E. Chem. Soc. Rev. 1990, 19, 83.
[2] Mayr, H.; Minegishi, S. Angew. Chem., Int. Ed. 2002, 41, 4493.
[3] Cowdrey, W. A.; Hughes, E. D.; Ingold, C. K.; Masterman, S.; Scott, A. D. J. Chem. Soc. 1937, 1252.
[4] Terrier, F. Modern Nucleophilic Aromatic Substitution, Wiley-VCH, Weinheim, 2013.
[5] (a) Smith, M.; March, J. March's Advanced Organic Chemistry, 6th ed., Wiley-Interscience, New York, 2007, p. 481. (b) Wells, P. R. Prog. Phys. Org. Chem. 1968, 6, 111.
[6] (a) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7. (b) Rapport, Z. Acc. Chem. Res. 1992, 25, 474. (c) Miller, S. I.; Yonan, P. K. J. Am. Chem. Soc. 1957, 79, 5931. (d) Modena, G. Acc. Chem. Res. 1971, 4, 73. (e) Miller, S. I. In Advances in Physical Organic Chemistry, Vol. 6, Ed.: Gold, V., Academic, New York, 1968, 185.
[7] (a) Bach, R. D.; Baboul, A. G.; Schlegel, H. B. J. Am. Chem. Soc. 2001, 123, 5787. (b) Lucchini, V.; Modena, G.; Pasquato, L. J. Am. Chem. Soc. 1995, 117, 2297.
[8] Glukhovtsev, M. N.; Pross, A.; Radom, L. J. Am. Chem. Soc. 1994, 116, 5961.
[9] Kim, C. K.; Hyun, K. H.; Kim, C. K.; Lee, I. J. Am. Chem. Soc. 2000, 122, 2294.
[10] (a) Marchese, G.; Naso, F.; Modena, G. J. Chem. Soc. B 1968, 958. (b) Marchese, G.; Naso, D.; Modena, G. J. Chem. Soc. B 1969, 290.
[11] Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Montanucci, M. Tetrahedron Lett. 1984, 25, 4975.
[12] (a) Hoffmann, R.; Radom, L.; Pople, J. A.; Schleyer, P. V. R.; Hehre, W. J.; Salem, L. J. Am. Chem. Soc. 1972, 94, 6221. (b) Apeloig Y.; Rappoport, Z. J. Am. Chem. Soc. 1979, 101, 5095. (c) Miller, S. I. Tetrahedron 1977, 33, 1211.
[13] (a) Ochiai, M.; Oshima, K.; Masaki, Y. J. Am. Chem. Soc. 1991, 113, 7059. (b) Ochiai, M.; Nishi, Y.; Hirobe, M. Tetrahedron Lett. 2005, 46, 1863.
[14] Okuyama, T.; Takino, T.; Sato, K.; Ochiai, M. J. Am. Chem. Soc. 1998, 120, 2275.
[15] Shiers, J. J.; Shipman, M.; Hayes, J. F.; Slawin, A. M. Z. J. Am. Chem. Soc. 2004, 126, 6868.
[16] Chiba, S.; Ando, K.; Narasaka, K. Synlett 2009, 2549.
[17] (a) Ando, K.; Kitamura, M.; Miura, K.; Narasaka, K. Org. Lett. 2004, 6, 2461. (b) Miyauchi, H.; Chiba, S.; Fukamizu, K.; Ando, K.; Narasaka, K. Tetrahedron 2007, 63, 5940.
[18] (a) Lei, M.-Y.; Fukamizu, K.; Xiao, Y.-J.; Liu, W.-M.; Twiddy, S.; Chiba, S.; Ando, K.; Narasaka, K. Tetrahedron Lett. 2008, 49, 4125. (b) Lei, M.-Y.; Xiao, Y.-J.; Liu, W.-M.; Fukamizu, K.; Chiba, S.; Ando, K.; Narasaka, K. Tetrahedron 2009, 65, 6888.
[19] Shen, S.-S.; Lei, M.-Y.; Wong, Y.-X.; Tong, M.-L.; Teo, P.; Chiba, S.; Narasaka, K. Tetrahedron Lett. 2009, 50, 3161.
[20] Casadei, M. A.; Galli, C.; Mandolini, L. J. Am. Chem. Soc. 1984, 106, 1051.
[21] Narasaka, K.; Kitamura, M. Eur. J. Org. Chem. 2005, 4505.
[22] Kusama, H.; Yamashuta, Y.; Narasaka, K. Chem. Lett. 1995, 5.
[23] Mori, S.; Uchiyama, K.; Hayashi, Y.; Narasaka, K.; Nakamura, E. Chem. Lett. 1998, 111.
[24] (a) Kusama, H.; Uchiyama, K.; Yamashita, Y.; Narasaka, K. Chem. Lett. 1995, 715. (b) Kusama, H.; Yamashita, Y.; Uchiyama, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 965. (c) Uchiyama, K.; Yoshida, M.; Hayashi, Y.; Narasaka, K. Chem. Lett. 1998, 607.
[25] (a) Yoshida, M.; Uchiyama, K.; Narasaka, K. Heterocycles 2000, 52, 681. (b) Kitamura, M.; Yoshida, M.; Kikuchi, T.; Narasaka, K. Synthesis 2003, 2415. (c) Tanaka, K.; Mori, Y.; Narasaka, K. Chem. Lett. 2004, 33, 26. (d) Kitamura, M.; Suga, T.; Chiba, S.; Narasaka, K. Org. Lett. 2004, 6, 4619.
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