Development of a one-pot sequential Sonogashira coupling for the synthesis of benzofurans

Tetrahedron

Volumn 64, Issue 37, 2008, Pages 8992-8996

  Csékei, Márton ^a   Novák, Zoltán ^a   Kotschy, András ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 TOLYL)BENZOFURAN; 2 (2' BROMOPHENYL)BENZOFURAN; 2 (4' METHOXYPHENYL)BENZOFURAN; 2 (4' NITROPHENYL)BENZOFURAN; 2 PHENYLBENZOFURAN; 5 BROMO 2 (4' METHOXYPHENYL)BENZOFURAN; 5 BROMO 2 (4' NITROPHENYL)BENZOFURAN; BENZOFURAN DERIVATIVE; HALIDE; NATURAL PRODUCT; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; VIGNAFURAN;

ARTICLE; COMPARATIVE STUDY; DEPROTECTION REACTION; DRUG SYNTHESIS; ONE POT SYNTHESIS; ORGANIC CHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS; SONOGASHIRA REACTION; STRUCTURE ANALYSIS;

EID: 48049087622     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.05.100     Document Type: Article

References (65)

1. Nicolaou K.C., Montagnon T., and Snyder S.A. Chem. Commun. (2003) 551
2. Tietze L.F., Brasche G., and Gericke K. Domino Reactions in Organic Synthesis (2006), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
3. Ho T.-L. Tandem Organic Reactions (1992), John Wiley & Sons, New York, NY
4. Müller T.J.J. Metal Catalyzed Cascade Reactions. Topics in Organometallic Chemistry 19 (2006)
5. Negishi E., and de Meijere A. Handbook of Organopalladium Chemistry for Organic Synthesis (2002), John Wiley & Sons, New York, NY
6. de Meijere A., and Diederich F. Metal-Catalyzed Cross-Coupling Reactions (2004), Wiley-VCH, Verlag GmbH & Co. KGaA, Weinheim
7. Tsuji J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century (2004), Wiley & Sons Ltd, Chichester, UK
8. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. (1975) 4467
9. Doucet H., and Hierso J.-C. Angew. Chem., Int. Ed. 46 (2007) 834
10. Chinchilla R., and Najera C. Chem. Rev. 107 (2007) 874
11. Novák Z., Szabó A., Répási J., and Kotschy A. J. Org. Chem. 68 (2003) 3327
12. Novák Z., and Kotschy A. Org. Lett. 5 (2003) 3495
13. Lindström S., Ripa L., and Hallberg A. Org. Lett. 2 (2000) 2291
14. Arcadi A., Cacchi S., Di Giuseppe S., Fabrizi G., and Marinelli F. Synlett (2002) 453
15. Sorensen U.S., and Pombo-Villar E. Tetrahedron 61 (2005) 2697
16. Yang C., and Nolan S.P. Organometallics 21 (2002) 1020
17. Kabalka G.W., Wang L., and Pagni R.M. Tetrahedron 57 (2001) 8017
18. Koseki Y., Omino K., Anzai S., and Nagasaka T. Tetrahedron Lett. 41 (2000) 2377
19. Nishihara Y., Ikegashira K., Hirabayashi K., Ando J., Mori A., and Hiyama T. J. Org. Chem. 65 (2000) 1780
20. Nishihara Y., Ikegashira K., Mori A., and Hiyama T. Chem. Lett. 12 (1997) 1233
21. Bleicher L., and Cosford N.D.P. Synlett (1995) 1115
22. Ley K.D., Li Y., Johnson J.V., Powell D.H., and Shanze K.S. Chem. Commun. (1999) 1749
23. Melissaris A., and Litt M.H. J. Org. Chem. 59 (1994) 5818
24. Ma L., Hu Q., and Pu L. Tetrahedron: Asymmetry 7 (1996) 3103
25. Novák Z., Nemes P., and Kotschy A. Org. Lett. 6 (2004) 4917
26. Csékei M., Novák Z., and Kotschy A. Tetrahedron 64 (2008) 975
27. D'Auria M. Synth. Commun. 22 (1992) 2393
28. Mio M.J., Kopel L.C., Braun J.B., Gidzikwa T.L., Hull K.L., Brisbois R.G., Markworth C.J., and Grieco P.A. Org. Lett. 4 (2002) 3199
29. Nagy A., Novák Z., and Kotschy A. J. Organomet. Chem. 690 (2005) 4453
30. Chow H., Wan C., Low K., and Yeung Y. J. Org. Chem. 66 (2001) 1910
31. Cacchi S., and Fabrizi G. Chem. Rev. 105 (2005) 2873
32. Arcadi A., Cacchi S., and Marinelli F. Synthesis (1986) 749
33. Kondo Y., Shiga F., Sakamoto T., and Yamanaka H. Tetrahedron 50 (1994) 11803
34. Nagamochi M., Fang Y.-Q., and Lautens M. Org. Lett. 9 (2007) 2955
35. Zhou C., Dubrovsky A.V., and Larock R.C. J. Org. Chem. 71 (2006) 1626
36. Arcadi A., Cacchi S., Del Rosario M., Fabrizi G., and Marinelli F. J. Org. Chem. 61 (1996) 9280
37. Larock R.C., and Yum E.K. J. Am. Chem. Soc. 113 (1991) 6689
38. Zeni G., and Larock R.C. Chem. Rev. 106 (2006) 4644
39. Cacchi S., Fabrizi G., and Goggiamani A. Curr. Org. Chem. 10 (2007) 1423
40. Yasuhara A., Kaneko M., and Sakamoto T. Heterocycles 48 (1998) 1793
41. Patil S., and Buolamwini J.K. Curr. Org. Chem. 3 (2006) 477
42. Novák Z., Timári G., and Kotschy A. Tetrahedron 59 (2003) 7509
43. Beutler U., Mazacek J., Penn G., Schenkel B., and Wasmuth D. Chimia 50 (1996) 154
44. Csékei M., Novák Z., Timári G., and Kotschy A. Arkivoc (2004) 285
45. Jinno S., Okita T., and Inouye K. Bioorg. Med. Chem. Lett. 9 (1999) 1029
46. Yao T., Yue D., and Larock R.C. J. Org. Chem. 70 (2005) 9985
47. Aslam S.N., Stevenson P.C., Phytian S.J., Veitch N.C., and Hall D.R. Tetrahedron 62 (2006) 4214
48. Sakai A., Aoyama S., and Shioiri T. Tetrahedron Lett. 40 (1999) 4211
49. Preston N.W., Chamberlain K., and Skipp R.A. Phytochemistry 14 (1975) 1875
50. Duffley R.P., and Stevenson R. J. Chem. Soc., Perkin Trans. 1 (1977) 802
51. Meyer M., Deschamps C., and Molho D. Bull. Soc. Chim. Fr. (1991) 91
52. Watanabe M., Kawanishi K., and Furukawa S. Chem. Pharm. Bull. 39 (1991) 579
53. Kinoshita T. Tetrahedron Lett. 38 (1997) 259
54. Hiroya K., Suzuki N., Yasuhara A., Egawa Y., Kasano A., and Sakamoto T. J. Chem. Soc., Perkin Trans. 1 (2000) 4339
55. Na M., Hoang D.M., Njamen D., Mbafor J.T., Fomun Z.T., Thuong P.T., Ahn J.S., and Oh W.K. Bioorg. Med. Chem. Lett. 17 (2007) 3868
56. Kinoshita T., and Ichinose K. Heterocycles 65 (2005) 1641
57. Yue D., Yao T., and Larock R.C. J. Org. Chem. 70 (2005) 10292
58. Arcadi A., Cacchi S., Fabrizi G., Marinelli F., and Moro L. Synlett (1999) 1432
59. Khalizadeh M.A., Hosseini A., Shokrollahzadeh M., Halvagar M.R., Ahmadi D., Mohannazadeh F., and Tajbakhsh M. Tetrahedron Lett. 47 (2006) 3525
60. Das B., Krishnaiah M., Wenkateswarlu K., and Reddy V.S. Tetrahedron Lett. 48 (2007) 81
61. Brenans P. Compte Rendues 192 (1931) 1037
62. Stetter H., and Siehnhold E. Chem. Ber. 88 (1955) 271
63. Hercouet A., and Le Corre M. Tetrahedron 37 (1981) 2867
64. Takeda N. Eur. J. Org. Chem. 9 (2007) 1491
65. Ono M., Kung M.P., Hou C., and Kung H.F. Nucl. Med. Biol. 29 (2002) 633