Stereoselective hydrohalogenation of alkynoic acids and their esters in ionic liquids

Journal of Chemical Research

Volumn , Issue 3, 2007, Pages 170-172

  Salazar, José ^a   Fernández, Francys ^a   Restrepo, Jelem ^a   López, Simón E ^a  

^a UNIVERSIDAD SIMÓN BOLÍVAR   (Venezuela)

Author keywords

Alkynoic acids; Hydrohalogenation; Ionic liquids; N alkylpyridinium

Indexed keywords

EID: 34249302424     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823407X200038     Document Type: Article

References (68)

1. (a) D.L. Romero, P.R. Manninen, F. Han and A.G. Romero, J. Org. Chem., 1999, 64, 4980;
2. (b) A.B. Smith and S.N. Kilenyl, Tetrahedron Lett., 1985, 26, 4419;
3. (c) R.C. Larock, K. Narayanan and S.S. Hernshberger, J. Org. Chem., 1983, 48, 4377;
4. (d) T. Yoshiyasa, I. Nobuyuki, A. Kazuo and S. Minora, Chem. Pharm. Bull., 1982, 30, 3167;
5. (e) G. Ege and H. Franz, J. Heterocyc. Chem., 1982, 19, 1267;
6. (f) P. Bey and J.P. Vevert, J. Org. Chem., 1980, 45, 3249;
7. (g) W. Oppolzer and C. Robbiani, Heb. Chim. Acta, 1980, 63, 2010;
8. (h) N. Miyaura, N. Sasaki, M. Itoh and A. Suzuki, Tetrahedron Lett., 1977, 3369.
9. (a) E.G. Stracker and G. Zweifel, Tetrahedron Lett., 1991, 32, 3329;
10. (b) A.O. King, N.J. Okukado and E. J. Negishi, J. Chem. Soc. Chem. Commun., 1977, 683.
11. (a) M. Abarbri, J.L. Parrain, J.C. Cintrat and A. Duchêne, Synthesis, 1996, 82;
12. (b) J.K. Stille and J.H. Simpson, J. Am. Chem. Soc., 1987, 109, 2138.
13. (a) V. Fiandanese, F. Babudri, G. Marchese and A. Punzi, Tetrahedron, 2002, 58, 9547;
14. (b) P. Beckström, U. Jacobson and T. Norin, Tetrahedron, 1988, 44, 2541;
15. (c) Y. Ikeda, J. Ukai, N. Ikeda and H. Yamamoto, Tetrahedron, 1987, 43, 743;
16. (d) F.D. Lewis, D.K. Howard, S.V. Barancyh and J.D. Oxman, J. Am. Chem. Soc., 1986, 108, 3016;
17. (e) B.M. Trost, T.N. Nanninga and D.M.T. Chan, Organometallics, 1982, 1, 1543.
18. (a) V. Fiandanese, D. Bottalico and G. Marchese, Tetrahedron, 2001, 57, 10213;
19. (b) I.E. Ronning and H.A. Frank, J. Food. Prot. 1988, 51, 651;
20. (c) P. Samuelson, Angew. Chem. int. Ed. Engl. 1983, 22, 805.
21. J. Cosseau, Synthesis, 1980, 805.
22. (a) P. Kropp, K. Daus, M. Tubergen, K. Kepler, V. Wilson, S. Craig and S. Crawford, J. Am. Chem. Soc., 1990, 112, 7433;
23. (b) P. Kropp, K. Daus, M. Tubergen, K. Kepler, V. Wilson, S. Craig, M. Bailargeon and G. Breton, J. Am. Chem. Soc., 1993, 115, 3071.
24. M. Periasamy and Ch. Reddy, Tetrahedron Lett. 1990, 31, 1919.
25. P. Campos, B. Garcia and M. Rodríguez, Tetrahedron Lett. 2002, 43, 6111.
26. Y. Ishii, N. Kamiya and Y. Chikami, Synlett, 1990, 675.
27. L. MacInnes, D. Schorstein and C. J. Suckling, Chem. Soc. Perkin Trans. 1, 1981, 1103.
28. (a) S. Ma and X. Lu, J. Chem. Soc. Chem. Commun., 1990, 1643;
29. (b) S. Ma and X. Lu, Tetrahedron Lett., 1990, 31, 7653;
30. (c) S. Ma, X Lu and Z. Li, J. Org. Chem., 1992, 57, 709;
31. (d) S. Ma and X. Lu, Chin. J. Chem., 1998, 16, 387;
32. (e) E. Piers, T. Wong, P. Coish and C. Rogers, Can. J. Chem., 1994, 72, 1816.
33. N. Urdaneta, J. Herrera, J. Salazar and S. Lopez, Synth. Commun., 2002, 32, 3003.
34. N. Urdaneta, J. Salazar, J. Herrera and S.E. Lopez, Synth. Commun., 2004, 34, 657.
35. For recent reviews see: (a) N. Jain, A. Kumar, S. Chauhan and S.M.S. Chauhan, Tetrahedron, 2005, 61, 1015;
36. (b) C. Baudequin, J. Baudoux, J. Levillain, D. Cahard, A.C. Gaumont and J.C. Plaquevent, Tetrahedron: Assymetry 2003, 14, 3081;
37. (c) H. Zhao and S.V. Malhotra. Aldrichimica Acta, 2002, 35, 75;
38. (d) H. Olivier-Bourbigou and L. Magna, J. Mol. Calai A: Chem., 2002, 182;
39. (e) M.J. Earle and K.R. Seddon, Pure Appl. Chem., 2000, 72, 1391;
40. (f) P. Wasserscheid and K. Wilhelm, Angew. Chem. Int. Ed., 2000, 39, 3772;
41. (g) T. Welton, Chem. Rev., 1999, 99, 2071.
42. M. Freemantle, Chem. Eng. News, 2001, 79, 36.
43. (a) I. Meracz and T. Oh, Tetrahedron Lett., 2003, 44, 6465;
44. (b) J. Wu, X. Wu, B. Beck and R.X. Ren, Tetrahedron Lett., 2002, 43, 387;
45. (c) J. Howarth, K. Hanlon, D. Fayne and P. McCormac, Tetrahedron Lett., 1997, 3097;
46. (d) J.A. Boon, J.A. Levisky, J.L. Pfluga and J.S. Wilkes, J. Org. Chem., 1986, 51, 480;
47. (e) J.K.D. Surette, L. Green and R.D. Singer, Chem. Commun., 1996, 2753;
48. (f) A.L. Monteiro, F.K. Zinn, R.F. de Souza and J. Dupont, Tetrahedron: Assymetry, 1997, 8, 177.
49. C. Patrascu, C. Sugisaki, C. Mingotaud, J.D. Marty, Y. Génisson and N. Lauth-de Viguerie, Heterocycles, 2004, 63, 2033;
50. (b) F.H. Hurley and T.P. Weir, J. Electrochem. Soc., 1951, 98, 203;
51. (c) R.J. Gale and R.A. Osteryoung, Inorg. Chem., 1980, 19, 2240;
52. (d) S. Tait and R.A. Osteryoung, Inorg. Chem., 1984, 23, 4352.
53. J. Salazar and R. Dorta, Synlet, 2004, 1318.
54. 2.3 as mild HF source has been published, see: H. Yoshino, K. Matsumoto, R. Hagiwara, Y. Ito, K. Oshima and S. Matsubara, J. Fluorine Chem. 2006, 127, 29;
55. 4]) ionic liquid and sodium halides was found to be an efficient halogenation system for the conversion of Baylis-Hillman adducts into (2Z)-2-(halomethyl)alk-2-enoates, see: T. Ying, W. Bao, Z. Wang and Y. Zhang, J. Chem. Res., 2005, 96.
56. (a) P.J. Kropp and S.D. Crawford, J. Org. Chem., 1994, 59, 3102;
57. (b) R.C. Fahey and D. Lee, J. Am. Chem. Soc., 1968, 90, 2124;
58. (c) P.F. Hudrlik, A.K. Kulkami, S. Jain and A.M. Hudrlik, Tetrahedron, 1983, 39, 877;
59. (d) G.F. Hennion and C.E. Welsh, J. Am. Chem. Soc., 1940, 62, 1367;
60. (e) K. Griesbaum and M. El-Abed, Chem. Ber., 1973, 106, 2001.
61. (a) K. Seddon and M. Deetlefs, Green Chem., 2003, 5, 181;
62. (b) T. Chan, M. Law and K. Wong, Green Chem., 2002, 4, 328.
63. R.J. Binnewirtz, H. Klingenberger, R. Weite and P. Paetzold, Chem. Ber., 1983, 116, 1271.
64. G.M. Zhuravlova, Zb. Aspirantsk and P. Odensk, Tekhnol. Inst. Kharch. Ta Kholodi'n Prom., 1963,1, 65;
65. Chem. Abs., 1965, 63: 31436.
66. H. Gershon and L. Schanks, J. Pharm. Sci., 1978, 67, 578.
67. J. Thiele and W. Peter, Ann., 1910, 369, 119.
68. M. Abarbri, J. Thibonnet, J.L. Parrain and A. Duchene, Synthesis, 2002, 543.