Copper-free Sonogashira cross-coupling reaction catalyzed by polymer-supported N-heterocyclic carbene palladium complex

Tetrahedron Letters

Volumn 48, Issue 40, 2007, Pages 7079-7084

  Kim, Jong Ho ^a   Lee, Dong Ho ^a   Jun, Bong Hyun ^a   Lee, Yoon Sik ^a  

^a Seoul National University   (South Korea)

Author keywords

Copper free; Heterogeneous catalysis; N Heterocyclic carbene (NHC); Palladium (Pd); Polymer supported catalyst; Sonogashira reaction

Indexed keywords

CARBENE; COPPER; HETEROCYCLIC COMPOUND; PALLADIUM COMPLEX; POLYMER;

ARTICLE; CATALYSIS; CATALYST; ENVIRONMENTAL TEMPERATURE; REACTION ANALYSIS; SONOGASHIRA REACTION;

EID: 34548454492     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.08.015     Document Type: Article

References (46)

1. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. 16 (1975) 4467
2. Sonogashira K., Yatake T., Tohda Y., Takahashi S., and Hagihara N. J. Chem. Soc., Chem. Commun. (1977) 291
3. Takahashi S., Kuroyama Y., Sonogashira K., and Hagihara N. Synthesis (1980) 627
4. Nicolaou K.C., and Dai W.M. Angew. Chem., Int. Ed. Engl. 30 (1991) 1387
5. Paterson I., Davies R.D.M., and Marquez R. Angew. Chem., Int. Ed. 40 (2001) 603
6. Kort M., Correa V., Valentijn A.R.P.M., Marel G.A., Potter B.V.L., Taylor C.W., and Boom J.H. J. Med. Chem. 43 (2000) 3295
7. Cosford N.D.P., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., and Varney M.A. J. Med. Chem. 46 (2003) 204
8. Brunsveld L., Meijer E.W., Prince R.B., and Moore J.S. J. Am. Chem. Soc. 123 (2001) 7978
9. Mongin O., Porres L., Moreaux L., Mertz J., and Blanchard-Desce M. Org. Lett. 4 (2002) 719
10. Mongin O., Papamicaël C., Hoyler N., and Gossauer A. J. Org. Chem. 63 (1998) 5568
11. Tobe Y., Utsumi N., Nagano A., and Naemura K. Angew. Chem., Int. Ed. 37 (1998) 1285
12. Onitsuka K., Fujimoto M., Ohshiro N., and Takahashi S. Angew. Chem., Int. Ed. 38 (1999) 689
13. Genet J.P., Blart E., and Savignac M. Synlett (1992) 715
14. Kabalka G.W., Wang L., Namboodiri V., and Pagni R.M. Tetrahedron Lett. 41 (2000) 5151
15. Fukuyama T., Shinmen M., Nishitani S., Sato M., and Ryu I. Org. Lett. 4 (2002) 1691
16. Powell N.A., and Rychnovsky S.D. Tetrahedron Lett. 37 (1996) 7901
17. Crisp G.T., Turner P.D., and Stephens K.A. J. Organomet. Chem. 570 (1998) 219
18. Nakamura K., Okubo H., and Yamaguchi M. Synlett (1999) 549
19. Choudary B.M., Madhi S., Chowdari N.S., Kantam M.L., and Sreedhar B. J. Am. Chem. Soc. 124 (2002) 14127
20. Köllhofer A., Pullmann T., and Plenio H. Angew. Chem., Int. Ed. 42 (2003) 1056
21. Faller J.W., Kultyshev R.G., and Parr J. Tetrahedron Lett. 44 (2003) 451
22. Böhm V.P.W., and Herrmann W.A. Eur. J. Org. Chem. (2000) 3679
23. Alonso D.A., Nájera C., and Pacheco M.C. Tetrahedron Lett. 43 (2002) 9365
24. Leadbeater N.E., and Tominack B.J. Tetrahedron Lett. 44 (2003) 8653
25. Soheili A., Albaneze-Walker J., Murry J.A., Dormer P.G., and Hughes D.L. Org. Lett. 5 (2003) 4191
26. Urganonkar S., and Verkade J.G. J. Org. Chem. 69 (2004) 5752
27. Arques A., Auňon D., and Molina P. Tetrahedron Lett. 45 (2004) 4337
28. Siemsen P., Livingston R.C., and Diederich F. Angew. Chem., Int. Ed. 39 (2000) 2632
29. Cheng J., Sun Y., Wang F., Guo M., Xu J.-H., Pan Y., and Zhang Z. J. Org. Chem. 69 (2004) 5428
30. Gelman D., and Buchwald S.L. Angew. Chem., Int. Ed. 42 (2003) 5993
31. Uozumi Y., and Kobayashi Y. Heterocycles 59 (2003) 71
32. Heuzé K., Méry D., Gauss D., and Astruc D. Chem. Commun. (2003) 2274
33. Djakovitch L., and Rollet P. Tetrahedron Lett. 45 (2004) 1367
34. Djakovitch L., and Rollet P. Adv. Synth. Catal. 346 (2004) 1782
35. Li P., Wang L., and Li H. Tetrahedron 61 (2005) 8633
36. Tyrrell E., Al-Saardi A., and Millet J. Synlett (2005) 487
37. Cwik A., Hell Z., and Figueras F. Tetrahedron Lett. 47 (2006) 3023
38. Li P.H., and Wang L. Adv. Synth. Catal. 348 (2006) 681
39. Nakai Y., Kimura T., and Uozumi Y. Synlett (2006) 3065
40. Kim J.H., Jun B.H., Byun J.W., and Lee Y.S. Tetrahedron Lett. 45 (2004) 5827
41. Kim J.H., Kim J.W., Shokouhimehr M., and Lee Y.S. J. Org. Chem. 70 (2005) 6714
42. Shokouhimehr M., Kim J.H., and Lee Y.S. Synlett (2006) 618
43. Weskamp T., Kohl F.J., Hieringer W., Gleich D., and Herrmann W.A. Angew. Chem., Int. Ed. 38 (1999) 2416
44. Schwarz J., Böhm V.P.W., Gardiner M.G., Grosche M., Herrmann W.A., Hieringer W., and Raudaschl-Sieber G. Chem. Eur. J. 6 (2000) 1773
45. 3O-C{double bond, long}C, benzene carbon). GC-MS: m/z 310.{A figure is presented}
46. 4 and evaporated under reduced pressure. The final product was isolated by column chromatography and identified by gas chromatography/mass spectroscopy (GC-MS) and nuclear magnetic resonance spectroscopy (NMR). The isolation yield was calculated from the mass value of the product.