Mild copper-catalyzed vinylation reactions of azoles and phenols with vinyl bromides

Chemistry - A European Journal

Volumn 12, Issue 20, 2006, Pages 5301-5313

  Taillefer, Marc ^a   Ouali, Armelle ^a   Renard, Brice ^a   Spindler, Jean Francis ^b  

^a INSTITUT CHARLES GERHARDT   (France)

^b Rhodia Europe   (France)

Author keywords

Catalysis; Copper; Homogeneous; Nitrogen heterocycles; Phenols; Vinylation

Indexed keywords

ALCOHOLS; COPPER COMPOUNDS; MOLECULAR STRUCTURE; SUBSTITUTION REACTIONS; SUBSTRATES;

COPPER-CATALYZED VINYLATION; HOMOGENEOUS; NITROGEN HETEROCYCLES; VINYLATION;

REACTION KINETICS;

EID: 33745908283     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501411     Document Type: Article

References (111)

1. a) H. A. A. El-Nabi, Tetrahedron 1997, 53, 1813-1822;
2. b) J. Firl, S. Sommer, Tetrahedron Lett. 1970, 1929-1932.
3. P. E. Maligres, M. M. Waters, J. Lee, R. A. Reamer, D. Askin, J. Org. Chem. 2002, 67, 1093-1101.
4. O. Fujimura, G. C. Fu, R. H. Grubbs, J. Org. Chem. 1994, 59, 4029-4031.
5. O. E. O. Hormi, L. Hirvelä, Tetrahedron Lett. 1993, 34, 6463-6466.
6. D. Gopal, Z. Rajagopalan, Tetrahedron Lett. 1987, 28, 5327-5330.
7. a) M. W. Briscoe, R. D. Chambers, S. J. Mullins, T. Nakamura, J. F. S. Vaughan, J. Chem. Soc. Perkin Trans. 1 1994, 21, 3119-3124;
8. b) A. E. Feiring, E. R. Wonchoba, J. Org. Chem. 1992, 57, 7014-7017;
9. Comprehensive Polymer Science, Vol. 3 (Ed.: G. Allen), Pergamon Press, New York, 1989.
10. a) S. J. Barker, R. C. Storr, J. Chem. Soc. Perkin Trans. 1 1990, 485-488;
11. b) A. Masquestiau, D. Beugnies, R. Flammang, A. R. Katritzky, M. Soleiman, T. Davis, J. N. Lam, J. Chem. Soc. Perkin Trans. 2 1988, 1071-1075;
12. P. A. Wender, C.B. Cooper, Tetrahedron 1986, 42, 2985-2991;
13. M. Märky, H. Schmidt, H.-J. Hansen, Helv. Chim. Acta 1979, 62, 2129-2153.
14. N. L. Mazyar, V. V. Annenkov, V. A. Klugova, S. M. Anan'ev, E. N. Danilovtseva. A. V. Rokhin, S. V. Zinchenko, Russ. Chem. Bull. 2000, 109, 2013-2017.
15. F. Brustolin, V. Castelvetro, F. Ciardelli, G. Rugged, A. Colligiani, J. Polym. Sci. A: Polym. Chem. 2001, 39, 253-262.
16. a) B. Iddon, D. J. Hartley, Tetrahedron Lett. 1997, 38, 4647-4650;
17. b) Y. L. Chen, K. G. Hedberg, K. J. Guarino, Tetrahedron Lett. 1989, 30, 1067-1068;
18. T. W. Green, P. G. M. Wuts, Protecting groups, 3rd ed., Wiley, New York, 1991, p. 619.
19. M. Ogata, H. Matsumhimizu, S. Kida, M. Shiro, K. Tawara, J. Med. Chem. 1987, 50, 1348-1354.
20. a) A. Ruland, W. Reuther, E. Ammermann, E.H. Pommer, BASF, DE 31130215, 1983
21. [Chem. Abstr. 1983, 98, 215596];
22. b) W. Reuther, A. Ruland, E. H. Pommer, BASF, EP 56125. 1982
23. [Chem. Abstr. 1982, 97, 216191] ;
24. B. Zeeh, E. Bucshmann, E. H. Pommer, BASF, EP 28363, 1981
25. [Chem. Abstr. 1981, 95, 150670].
26. U. Kratz, K. Luerssen, Bayer, EP 297393 A2, 1989
27. [Chem. Abstr. 1989, 110, 231640].
28. For the synthesis of N-alkenylazoles, see: a) E. Abele, O. Dzenitis, K. Rubina, E. Lukevics, Chem. Heterocycl. Compd. 2002, 38, 682-685;
29. b) B. Iddon, D. J. Hartley, Tetrahedron Lett. 1997, 38, 4647-4650;
30. T. Kakimoto, JP 04021672 A2, 1992
31. [Chem. Abstr. 1992, 116, 235635];
32. M. Märky, H. Schmidt, H.-J. Hansen, Helv. Chim. Acta 1979, 62, 2129-2153;
33. e) G. Cooper, W. J. Irwin, Chem. Soc. Perkin Trans. 1 1976, 798-803;
34. f) G. Cooper, W. J. Irwin, J. Chem. Soc. Perkin Trans. 1 1976, 545-549;
35. g) G. Cooper, W. J. Irwin, J. Chem. Soc. Perkin Trans. l 1976, 75-80. For the synthesis of alkenyl aryl ethers, see:
36. h) J. Ying, N. L. Bauld, J. Org. Chem. 1999, 64, 9251-9253.
37. For the synthesis of W-alkenylazoles, see: a) E. Diez-Barra, A. de la Hoz, A. Loupy, A. Sanchez-Migallon, Heterocydes 1994, 38, 1367-1374;
38. b) A. R. Katritzky, J. Li, N. Malhotra, Ann. Chem. 1992, 843-853;
39. E. Diez-Barra, A. de la Hoz, A. Loupy, A. Sanchez-Migallon, Heterocydes 1994, 38, 1367-1374. For the synthesis of alkenyl aryl ethers, see:
40. M. Julia, M. Baillargue, Bull. Soc. Chim. Fr. 1966, 734-745;
41. e) C. C. Price, W. H. Snyder, J. Am. Chem. Soc. 1961, 83, 1773.
42. a) M. Urbala, N. Kuznik, S. Krompiec, J. Rzepa, Synlett 2004, 1203-1206;
43. b) J. V. Crivello, S. Kong, J. Org. Chem. 1998, 63, 6745-6748;
44. P. Golborn, F. Scheinmann, J. Chem. Soc. Perkin Trans. 1 1973, 2870-2875;
45. P. W. Jolly, F. G. A. Stone, K. Mackensie, J. Chem. Soc. 1965, 6416-6420.
46. For the synthesis of N-alkenylazoles, see: a) B. A. Trofimov, O.A. Tarasova, M. A. Shemetova, A. V. Afonin, L. V. Klyba, L. V. Baikalova, A. I. Mikhaleva, RUSS. J. Org. Chem. 2003, 39, 408-414, and references therein ;
47. b) B. A. Trofimov, O. A. Tarasova, A. I. Mikhaleva, N. A. Kalinina, L. M. Sinegovskaya, J. Henkelmann, Synthesis 2000, 11, 1585-1589;
48. B.J.J. Aiscar, J. Henkelmann, T. Preiss, P. Knochel, D. Tzalis, C. Koradin, EP 1055653 A2, 2000
49. [Chem. Abstr. 2000, 134, 17163];
50. D. Tzalis, C. Koradin, P. Knochel, Tetrahedron Lett. 1999, 40, 6193-6195;
51. e) T. G. Ermakova, N. P. Kuznetsova, L. A. Tatarova, V. N. Kurochkni, RU 2030406 Cl, 1995
52. [Chem. Abstr. 1995, 124, 117324];
53. f) P. Bourgeois, J. Lucrece, J. Heterocycl. Chem. 1978, 15, 1543-1545.
54. For the synthesis of alkenyl aryl ethers, see: W. Reppe, Ann. Chem. 1956, 607, 84-111.
55. a) D. P. M. Pleynet, J. K. Dutton, A. P. Johnson, Tetrahedron 1999, 55, 11903-11926;
56. b) A. R. Katritzky, D. Toader, L. Xie, Synthesis 1996, 1425-1427;
57. A. P. Johnson, J. K. Dutton, D. P. M. Pleynet, Heterocydes 1994, 37, 1913-1932;
58. A. R. Katritzky, J. N. Lam, Heteroat. Chem. 1990, 1, 21-31;
59. e) A. R. Katritzky, R. J. Offerman, P. Catildo, M. Soleiman, Red. Trav. Chim. Pays-Bas 1988, 107, 641 -645.
60. L. Maier, G. Rist, Phosphorus Sulfur Relat. Elem. 1987, 32, 65-72.
61. H. Qian, X. Huang, Synth. Commun. 2000, 30, 1413-1417.
62. a) S. Surprenant, W. Y. Chan, C. Berthelette, Org. Lett. 2003, 5, 4851-4854;
63. b) G. Wittig, W. Boell, K. Walter, H. Karl, Ber. 1962, 95, 2514-2525.
64. For acid-catalyzed vinylation, see: a) V. N. Kizhnyaev, F. A. Pokatilov, N. A. Tsypina, G. V. Ratovskii, L. I. Vereshchagin, A. I. Smirnov, RUSS. J. Org. Chem. 2002, 38, 1056-1059;
65. b) Y. L. Chen, K. G. Hedberg. K.J. Guarino, Tetrahedron Lett. 1989, 30, 1067-1068;
66. G. V. Shatalov, V. D. Galkin, O. V. Voishcheva, Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 1976, 19, 1507-1510;
67. for base-catalyzed vinylation, see: J. Henkelmann, M. Heider, T. Ruehl, EP 752422 AI, 1997
68. [Chem. Abstr. 1997. 726, 117979]
69. A. Y. Lebedev, V. V. Izmer, D. N. Kazyul'kin, I. P. Beletskaya, A. Z. Voskoboynikov, Org. Lett. 2002, 4, 623-626.
70. M. C. Willis, D. Taylor, A. T. Gillmore, Chem. Commun. 2003, 2222-2223.
71. For the synthesis of N-alkenylazoles and alkenyl aryl ethers, see: a) P. Y. S. Lam, G. Vincent, D. Bonne, C. G. Clark, Tetrahedron Lett. 2003, 44, 4927-4931;
72. b) P. Y. S. Lam, G. Vincent, C. G. Clark, S. Deudon, P. K. Jadhav, Tetrahedron Lett. 2001, 42, 3415-3418.
73. M. Blouin, R. Frenette, J. Org. Chem. 2001, 66, 9043-9045.
74. Z. Wan, C. D. Jones, T. M. Koenig, Y. J. Pu, D. Mitchell, Tetrahedron Lett. 2003, 44, 8257-8259.
75. D. Ma, Q. Cai, X. Xie, Synlett 2005, 11, 1767-1770.
76. For leading references, see: a) X. Pan, Q. Cai, D. Ma, Org. Lett. 2004, 6, 1809-1812;
77. b) L. Jiang, G. E. Job, A. Klapars, S. L. Buchwald, Org. Lett. 2003, 5, 3667-3669.
78. For patents, see: a) M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, FR 2833947, 2003
79. [Chem. Abstr. 2003, 139, 69290];
80. b) M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, WO 03/050885, 2003;
81. M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, FR 2840303, 2003
82. [Chem. Abstr. 2004, 140, 16744];
83. M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, A. Ouali, WO 03/101966, 2003;
84. e) M. Taillefer, H.-J. Cristau, P.P. Cellier, J.-F. Spindler, FR 0310253, 2004;
85. f) J.-F. Spindler, M. Taillefer, H.-J. Cristau, P.P. Cellier, A. Ouali, WO 2005023731, 2005.
86. For applications of our copper-based catalytic systems, see: a) H.-J. Cristau, A. Ouali, J.-F. Spindler, M. Taillefer, Chem. Eur. J. 2005, 11, 2483-2492;
87. b) H.-J. Cristau, P. P. Cellier, J.-F. Spindler, M. Taillefer, Org. Lett. 2004, 6, 913-916;
88. H.-J. Cristau, P. P. Cellier, J.-F. Spindler, M. Taillefer, Eur. J. Org. Chem. 2004, 695-709;
89. H.-J. Cristau, P. P. Cellier, J.-F. Spindler, M. Taillefer, Chem. Eur. J. 2004, 10, 5607-5622.
90. The ability of one of our copper-based catalysts to afford vinylation reactions was shown in a particular case (N-vinylation of pyrazole) but the reaction conditions were, however, not optimized.
91. J. Clayden, N. Greeves, S. Warren, P. Wothers, Chimie Organique, de Boeck, Paris, 2003, p. 493.
92. Since Z-β-bromostyrene also led to the formation of byproducts whatever the nature of the nitrogen heterocycle, the yields of E-βstyrylazoles given in Table 1 are expressed with respect to E-β-bromostyrene.
93. a) J. A. Joule, K. Mills, G. F. Smith, Heterocyclic Chemistry, 3rd ed., Stanley Thornes, Oxford, 1995, p. 394;
94. b) J. Elguero, Comprehensive Heterocydic Chemistry, Vol. 5, 1st ed., (Eds.: A. R. Katritzky, C. W. Rees), Pergamon Press, Oxford, 1984, pp. 211-213;
95. A. N. Kost, I.I. Grandberg, Advances in Heterocydic Chemistry, Vol. 6, (Eds.: A. R. Katritzky, A. J. Boulton), Academic Press, New York, 1966, pp. 353-355.
96. J. Elguero, R. Jacquier, J. Chim. Phys. 1966, 63, 1242-1246.
97. a)J. Elguero, A. Fruchier, R. Jacquier, Bull. Soc. Chim. Fr. 1966, 2075-2084;
98. b) J. Elguero, A. Fruchier, R. Jacquier, U. Scheidegger, J. Chim. Phys. 1971, 1113-1121.
99. F. TomÁs, J. M. Abboud, J. Laynez, R. Notario, L. Santos, S. O. Nilsson, J. Catalan, R. M. Claramunt, J. Elguero, j. Am. Chem. Soc. 1989, 111, 7348-7353.
100. Yield based on the initial E/Z mixture.
101. C. G. Bates, P. Saejueng, D. Venkataraman, Org. Lett. 2004, 6, 1441-1444.
102. a) E. Buck, Z. J. Song, D. Tschaen, P. G. Dormer, R. P. Volante, P. J. Reider, Org. Lett. 2002, 4, 1623-1626;
103. b) R. K. Gujadhur, D. Venkataraman, Synth. Commun. 2001, 31, 2865-2879;
104. A. A. Moroz, M. S. Shvartsberg, Russ. Chem. Rev. 1974, 43, 679-689.
105. A. Jutand, S. Negri, Organometallics 2003, 22, 4229-4237.
106. R. K. Dieter, L. A. Silks III, J. R. Fishpaugh, M. E. Kastner, J. Am. Chem. Soc. 1985, 707, 4679-4692.
107. D. D. Perrin, W. L. F. Armarego, D. R. Perrin, Purification of Laboratory Chemicals, 3rd ed., Pergamon Press, New York, 1985.
108. L. Maier, G. Rist, Phosphorus Sulfur Relat. Elem. 1987, 32, 65-72.
109. H. Gross, S. Beisert, B. Costisella, j. Prakt. Chem. 1981, 323, 877-886.
110. A. R. Katritzky, S. Rachwal, K. C. Caster, F. Mahni, J. Chem. Soc. Perkin Trans. 1 1987, 781 -789.
111. S. Trofimenko, J. Org. Chem. 1970, 55, 3459-3462.