Cyclopalladated ferrocenylimines: efficient catalysts for homocoupling and Sonogashira reaction of terminal alkynes

Tetrahedron

Volumn 63, Issue 9, 2007, Pages 1963-1969

  Yang, Fan ^a   Cui, Xiuling ^a   Li, Ya nan ^a   Zhang, Jinli ^a   Ren, Ge rui ^a   Wu, Yangjie ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

Cyclopalladated ferrocenylimine; Homocoupling; Sonogashira reaction; Terminal alkynes

Indexed keywords

ALKYNE; AMINE; BROMINE DERIVATIVE; CHLORIDE; FERROCENE DERIVATIVE; FUNCTIONAL GROUP; IODINE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SONOGASHIRA REACTION; TERMINAL SEQUENCE;

EID: 33846358874     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.064     Document Type: Article

References (70)

1. Bohlmann F., Burkhart F.T., and Zero C. Naturally Occurring Acetylenes (1973), Academic, London and New York, NY
2. Hunstman V.D. In: Patai S. (Ed). The Chemistry of the Carbon-Carbon Triple Bond (1978), Wiley-Interscience, London 553-620
3. Paterson I., Davies R.D., and Marquez R. Angew. Chem., Int. Ed. 40 (2001) 603
4. Sonogashira K. J. Organomet. Chem. 653 (2002) 46
5. Negishi E., and Anastasia L. Chem. Rev. 103 (2003) 1979
6. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4442
7. For representative reviews on palladium-catalyzed homocoupling reactions of alkynes, see:
8. Siemsen P., Livingston R.C., and Diederich F. Angew. Chem., Int. Ed. 39 (2000) 2632
9. Negishi E., and Alimardanov A. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1 (2002), Wiley-Interscience, New York, NY 989
10. For representative reviews on palladium-catalyzed Sonogashira reactions of alkynes, see:
11. Sonogashira K. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 3 (1991), Pergamon, New York, NY 521-549
12. Rossi R., Carpita A., and Bellina F. Org. Prep. Proced. Int. 27 (1995) 129
13. Tsuji J. Palladium Reagents and Catalysts (1995), Wiley, Chichester, UK pp 168-171
14. Nicolaou K.C., and Sorensen E.J. Classics in Total Synthesis (1996), VCH, Weinheim, Germany pp 582-586
15. Brandsma L., Vasilevsky S.F., and Verkruijsse H.D. Application of Transition Metal Catalysts in Organic Synthesis (1998), Springer, Berlin pp 179-225
16. Sonogashira K. In: Diederich F., and Stang P.J. (Eds). Metal-Catalyzed Cross-Coupling Reactions (1998), Wiley-VCH, Weinheim, Germany 203-229
17. For palladium-catalyzed homocoupling of alkynes, see:
18. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. 16 (1975) 4467
19. Vlassa M., Ciocan-Tarta I., Margineanu F., and Oprean I. Tetrahedron 52 (1996) 1337
20. Li J., Mau A.W.-H., and Strauss C.R. Chem. Commun. (1997) 1275
21. Li J., and Jiang H. Chem. Commun. (1999) 2369
22. Chao D.H., Lee J.H., and Kim B.H. J. Org. Chem. 66 (1999) 8480
23. Lei A., Srivastava M., and Zhang X. J. Org. Chem. 67 (2002) 1969
24. Li J.-H., Liang Y., and Xie Y.-X. J. Org. Chem. 70 (2005) 4393
25. Li J.-H., Liang Y., and Zhang X.-D. Tetrahedron 61 (2005) 1903
26. Shi M., and Qian H.-X. Appl. Organomet. Chem. 20 (2006) 771
27. Batsanov A.S., Collings J.C., Fairlamb I.J.S., Holland J.P., Howard J.A.K., Lin Z.-Y., Marder T.B., Parsons A.C., Ward R.M., and Zhu J. J. Org. Chem. 70 (2005) 703
28. For selected papers on the palladium/phosphine/CuI/amine system for the Sonogashira cross-coupling reactions, see:
29. Hundertmark T., Litter A.F., Buchwald S.L., and Fu G.C. Org. Lett. 2 (2000) 1729
30. Chow H.-F., Wan C.-W., Low K.-H., and Yeung Y.-Y. J. Org. Chem. 66 (2001) 1910
31. Novák Z., Szabó A., Répási J., and Kotschy A. J. Org. Chem. 68 (2003) 3327
32. Hierso J.-C., Fihri A., Amardeil R., and Meunier P. Org. Lett. 6 (2004) 3473
33. Son S.U., Jang Y., Park J., Na H.B., Park H.M., Yun H.J., Lee J., and Hyeon T. J. Am. Chem. Soc. 126 (2004) 5026
34. Adjabeng G., Brenstrum T., Frampton C.S., Robertson A.J., Hillhous J., McNulty J., and Capretta A. J. Org. Chem. 69 (2004) 5082
35. Shao L.-X., and Shi M. J. Org. Chem. 70 (2005) 8635
36. For recent papers on palladium-catalyzed Sonogashira reaction under copper free conditions, see:
37. Leadbeater N.E., and Tominack B.J. Tetrahedron Lett. 44 (2003) 8653
38. Liang B., Dai M., Chen J.-H., and Yang Z. J. Org. Chem. 70 (2005) 391
39. Gholap A.R., Venkatesan K., Pasricha R., Daniel T., Lahoti R.J., and Srinivasan K.V. J. Org. Chem. 70 (2005) 4869
40. Li P.-H., Wang L., and Li H.-J. Tetrahedron 61 (2005) 8633
41. Shirakawa E., Kitabata T., Otsuka H., and Tsuchimoto T. Tetrahedron 61 (2005) 9878
42. Liang Y., Xie Y.-X., and Li J.-H. J. Org. Chem. 71 (2006) 379
43. Yi C.-Y., and Hua R.-M. J. Org. Chem. 71 (2006) 2535
44. Glaser C. Ber. Dtsch. Chem. Ges. 2 (1869) 422
45. Hay A.S. J. Org. Chem. 27 (1962) 3320
46. Rossi R., Carpita A., and Begelli C. Tetrahedron Lett. 26 (1985) 523
47. Liu Q., and Burton D.J. Tetrahedron Lett. 38 (1997) 371
48. For representative reviews, see:
49. Bedford R.B. Chem. Commun. (2003) 1787
50. Herrmann W.A., Ofele K., and Preysing D.V. J. Organomet. Chem. 687 (2003) 229
51. Bedford R.B., Cazin C.S.J., and Holder D. Coord. Chem. Rev. 248 (2004) 2283
52. Beletskaya J.P., and Cheprakov A.V. J. Organomet. Chem. 689 (2004) 4055
53. Alonso D.A., Nájera C., and Pacheco M.C. Adv. Synth. Catal. 345 (2003) 1146
54. Consorti C.S., Flore F.R., Rominger F., and Dupont J. Adv. Synth. Catal. 348 (2006) 133
55. For the preparation of the cyclopalladated ferrocenylimines, see:. Huo S.-Q., Wu Y.-J., Du C.-X., Zhu Y., Yuan H.-Z., and Mao X.-A. J. Organomet. Chem. 483 (1994) 139
56. Yadav V.K., and Babu K.G. J. Org. Chem. 69 (2004) 577
57. Wu S.-T., Finkenzeller U., and Reiffenrath V. J. Appl. Phys. 65 (1989) 4372
58. Rodríguez J.G., Martín-Villamil R., Cano F.H., and Fonseca I. J. Chem. Soc., Perkin Trans. 1 (1997) 709
59. Paquett L.A., and Wittenbrook L.S. J. Am. Chem. Soc. 89 (1967) 4483
60. Alagille D., Baldwin R.M., Roth B.L., Wroblewski J.T., Grajkowska E., and Tamagnan G.D. Bioorg. Med. Chem. 13 (2005) 197
61. Jacques J. Ger. Offen. (1972) 18
62. Cheng J., Sun Y.-H., Wang F., Guo M.-J., Xu J.-H., Pan L., and Zhang Z.-G. J. Org. Chem. 69 (2004) 5428
63. Spadlo A., Dabrowski R., Filipowicz M., Stolarz Z., Przedmojski J., Gauza S., Fan C.Y.H., and Wu S.-T. Liq. Cryst. 30 (2003) 191
64. Yoshida K., and Fueno T. J. Org. Chem. 38 (2003) 1045
65. Arcadi A., Cacchi S., Fabrizi G., Marinelli F., and Pace P. Eur. J. Org. Chem. 12 (1999) 3305
66. Agawa T., and Miller S.I. J. Am. Chem. Soc. 83 (1961) 449
67. Mori Y., and Seki M. J. Org. Chem. 68 (2003) 1517
68. Van den Hoven B.G., and Alper H. J. Org. Chem. 64 (1999) 9640
69. Gil-Moltó J., Karlström S., and Nájera C. Tetrahedron 61 (2005) 12168
70. Katritzky A.R., Abdel-Fattah A.A.A., and Wang M.-Y. J. Org. Chem. 67 (2002) 7526