PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation

Tetrahedron

Volumn 63, Issue 36, 2007, Pages 8855-8871

  Valeur, Eric ^a   Bradley, Mark ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

Amidation; Amide; Amide bond formation; Coupling reagent; IIDQ; Immobilized reagent; Parallel synthesis; Polymer supported reagent

Indexed keywords

1,2,3,4 TETRAHYDRO NAPHTHALEN 1 YLAMINE; 4 TERT BUTYLANILINE; AMINE; ANILINE DERIVATIVE; BENZYLAMINE; CARBOXYLIC ACID; MORPHOLINE; POLYSTYRENE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPARATIVE STUDY; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 34447623583     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.06.019     Document Type: Article

References (39)

1. Ley S.V., Baxendale I.R., Bream R.N., Jackson P.S., Leach A.G., Longbottom D.A., Nesi M., Scott J.S., Storer R.I., and Taylor S.J. J. Chem. Soc., Perkin Trans. 1 (2000) 3815-4195
2. Kirschning A., Monenschein H., and Wittenberg R. Angew. Chem., Int. Ed. 40 (2001) 650-679
3. Bhalay G., Dunstan A., and Glen A. Synlett (2000) 1846-1859
4. See for example:. Desai M.C., and Stephens Stramiello L.M. Tetrahedron Lett. 34 (1993) 7685-7688
5. See for example:. Zhang M., Vedantham P., Flynn D.L., and Hanson P.R. J. Org. Chem. 69 (2004) 8340-8344
6. Chinchilla R., Dodsworth D.J., Najera C., and Soriano J.M. Tetrahedron Lett. 41 (2000) 2463-2466
7. Filip S.V., Lejeune V., Vors J.-P., Martinez J., and Cavelier F. Eur. J. Org. Chem. 9 (2004) 1936-1939
8. Carpino L.A. J. Am. Chem. Soc. 115 (1993) 4397-4398
9. Albericio F., Bofill J.M., El-Faham A., and Kates S.A. J. Org. Chem. 63 (1998) 9678-9683
10. Albericio F., Cases M., Alsina J., Triolo S.A., Carpino L.A., and Kates S.A. Tetrahedron Lett. 38 (1997) 4853-4856
11. Tung R.D., and Rich D.H. J. Am. Chem. Soc. 107 (1985) 4342-4343
12. Belleau B., Martel R., Lacasse G., Menard M., Weinberg N.L., and Perron Y.G. J. Am. Chem. Soc. 90 (1968) 823-824
13. Belleau B., and Malek G. J. Am. Chem. Soc. 90 (1968) 1651-1652
14. Valeur E., and Bradley M. Chem. Commun. (2005) 1164-1166
15. Delgado M., and Janda K.D. Curr. Org. Chem. 6 (2002) 1031-1043
16. Boissonnas R.A., Guttmann S., Jaquenoud P.A., and Waller J.P. Helv. Chim. Acta 38 (1955) 1491-1501
17. Van der Auwera C., Van Damme S., and Anteunis M.J.O. Int. J. Pept. Protein Res. 29 (1987) 464-471
18. PS-IIDQ is now commercially available from Novabiochem (01-64-0469) and Polymer Laboratories (PL-IIDQ).
19. Perreux L., Loupy A., and Volatron F. Tetrahedron 58 (2002) 2155-2162
20. Heyde C., Zug I., and Hartmann H. Eur. J. Org. Chem. (2000) 3273-3278
21. Yin J., and Buchwald S.L. Org. Lett. 2 (2000) 1101-1104
22. Acheson R.M., and Harvey C.W.C. J. Chem. Soc., Perkin Trans. 1 (1976) 465-470
23. Park S.-D., Oh J.-H., and Lim D. Tetrahedron Lett. 43 (2002) 6309-6311
24. Badr M.Z.A., Aly M.M., Mahgoub S.A., Fahmy A.M., and Atallah A.A. Bull. Chem. Soc. Jpn. 61 (1988) 1779-1783
25. Tillack A., Rudloff I., and Beller M. Eur. J. Org. Chem. (2001) 523-528
26. Dondoni A., Perrone D., and Semola T. Synthesis 2 (1995) 181-186
27. Albericio F., Bailen M.A., Chinchilla R., Dodsworth D.J., and Najera C. Tetrahedron 57 (2001) 9607-9613
28. Zhang R., and Madalengoita J.S. Tetrahedron Lett. 37 (1996) 6235-6239
29. Obrecht D., and Heimgartner H. Helv. Chim. Acta 70 (1987) 102-115
30. Wintner E.A., Conn M.M., and Rebek Jr. J. J. Am. Chem. Soc. 116 (1994) 8877-8884
31. Lee C.K., Yu J.S., and Ji Y.R. J. Heterocycl. Chem. 39 (2002) 1219-1227
32. Wipf P., and Heimgartner H. Helv. Chim. Acta 70 (1987) 354-368
33. Ogawa T., Hikasa T., Ikegami T., Ono N., and Suzuki H. J. Chem. Soc., Perkin Trans. 1 (1994) 3473-3478
34. Koh H.J., Kim T.H., Lee B.-S., and Lee I. J. Chem. Res. 11 (1996) 2741-2751
35. Baker B.R., and Hurlbut J.A. J. Med. Chem. 10 (1967) 1129-1133
36. Frkanec L., Visnjevac A., Kojic-Prodic B., and Zinic M. Chem.-Eur. J. 6 (2000) 442-453
37. Abraham D.J., Gazze D.M., Kennedy P.E., and Mokotoff M. J. Med. Chem. 12 (1984) 1549-1559
38. Yoshikawa K., and Achiwa K. Chem. Pharm. Bull. 43 (1995) 2048-2053
39. Kiso Y., and Yajima H. Chem. Commun. (1972) 942-943