First Heck reaction with arenediazonium cations with recovery of Pd-triolefinic macrocyclic catalyst

Organic Letters

Volumn 5, Issue 9, 2003, Pages 1559-1561

  Masllorens, Judit ^a   Moreno Mañas, Marcial ^b   Pla Quintana, Anna ^a   Roglans, Anna ^a  

^a UNIVERSITY OF GIRONA   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BORIC ACID; CATION; DIAZONIUM COMPOUND; MACROCYCLIC COMPOUND; PALLADIUM; PHOSPHINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

AIR; ARTICLE; CATALYST; HECK REACTION; MOISTURE; ROOM TEMPERATURE;

EID: 0037644428     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034340b     Document Type: Article

References (38)

1. (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Heck, R. F. Org. React. N.Y. 1982, 27, 345.
2. (b) Heck, R. F. Org. React. N.Y. 1982, 27, 345.
3. (c) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, New York, 1991; Vol. 4, pp 833-863.
4. (d) De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
5. (e) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
6. (f) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.; Liu, F. Chem. Rev. 1996, 96, 365.
7. (g) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427.
8. (h) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
9. (i) Whitcombe, N. J.; Kuok Hii, K.; Gibson, S. E. Tetrahedron 2001, 57, 7449.
10. (j) Beller, M.; Zapf, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; Vol. 1, pp 1209-1222.
11. (a) Cerezo, S.; Cortés, J.; Lago, E.; Molins, E.; Moreno-Mañas, M.; Parella, T.; Pleixats, R.; Torrejón, J.; Vallribera, A. Eur. J. Inorg. Chem. 2001, 1999.
12. (b) Cortés, J.; Moreno-Mañas, M.; Pleixats, R. Eur. J. Org. Chem. 2000, 239.
13. (c) Llobet, A.; Masllorens, E.; Moreno-Mañas, M.; Pla-Quintana, A. ; Rodríguez, M.; Roglans, A. Tetrahedron Lett. 2002, 43, 1425.
14. (a) Estrine, B.; Blanco, B.; Bouquillon, S.; Hénin, F.; Moreno-Mañas, M.; Muzart, J.; Pena, C.; Pleixats, R. Tetrahedron Lett. 2001, 42, 7055.
15. (b) Moreno-Mañas, M.; Pleixats, R.; Spengler, J.; Chevrin, C.; Estrine, B.; Bouquillon, S.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A. Eur. J. Org. Chem. 2003, 274.
16. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Moreno-Mañas, M.; Vallribera, A. Tetrahedron Lett. 2002, 43, 5537.
17. (a) Kikukawa, K.; Matsuda, T. Chem. Lett. 1977, 159.
18. (b) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.
19. (c) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T. Chem. Lett. 1988, 873.
20. (d) Yong, W.; Yi, P.; Zhuangyu, Z.; Hongwen, H. Synthesis 1991, 967.
21. (e) Sengupta, S.; Bhattacharya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943.
22. (f) Beller, M.; Fischer, H.; Kühlein, K. Tetrahedron Lett. 1994, 35, 8773.
23. (g) Beller, M.; Kühlein, K. Synlett 1995, 441.
24. (h) Sengupta, S.; Sadhukhan, S. K. Tetrahedron Lett. 1998, 39, 715.
25. (i) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J. P. Tetrahedron Lett. 1999, 40, 4815.
26. (j) Priego, J.; Carretero, J. C. Synlett 1999, 1603.
27. (k) Darses, S.; Pucheault, M.; Genêt, J. P. Eur. J. Org. Chem. 2001, 1121.
28. (l) Carpes, M. J. S.; Correia, C. R. D. Tetrahedron Lett. 2002, 43, 741.
29. (m) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079.
30. (n) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
31. Electrospray Ionization Mass Spectrometry. Fundammentals, Instrumentation and Applications; Cole, R. B., Ed.; John Wiley & Sons: New York, 1997.
32. (a) Wilson, S. R.; Pérez, J.; Pasternak, A. J. Am. Chem. Soc. 1993, 115, 1994.
33. (b) Aliprantis, A. O.; Canary, J. W. J. Am. Chem. Soc. 1994, 116, 6985.
34. (c) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147.
35. (d) Brown, J. M.; Hii, K. K. Angew. Chem., Int. Ed. Engl. 1996, 35, 657.
36. (e) Hii, K. K.; Claridge, T. D. W.; Brown, J. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984.
37. (f) Aramendía, M. A.; Lafont, F.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. J. Org. Chem. 1999, 64, 3592.
38. (g) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J. O. Angew. Chem., Int. Ed. 2002, 41, 2738.