Polymer-bound triphenylphosphine as traceless reagent for Mitsunobu reactions in combinatorial chemistry: Synthesis of aryl ethers from phenols nad alcohols

Tetrahedron Letters

Volumn 39, Issue 48, 1998, Pages 8751-8754

  Tunoori, Ashok Rao ^a   Dutta, Dinah ^a   Georg, Gunda I ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKYL ARYL ETHER; DICARBOXYLIC ACID; PHENOL DERIVATIVE; PHOSPHINE DERIVATIVE; POLYMER; REAGENT;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FILTRATION; PURIFICATION; SYNTHESIS;

EID: 0032569908     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01988-1     Document Type: Article

References (16)

1. 1. For review: Bunin, B. A. The Combinatorial Index; ; Academic: San Diego, 1998.
2. 2. For review: Wilson, S. R.; Czarnik, A. W. Combinatorial Chemistry: Synthesis and Application; Wilson, S. R.; Czarnik, A. W., Ed.; Wiley: New York, 1997.
3. 3. For review: Mitscher, L. A. Chemtracts-Org. Chem. 1995, 8, 19.
4. 4. For review: Fecik, R. A.; Frank, K. E.; Gentry, E. J.; Menon, S. R.; Mitscher, L. A.; Telikapali, H. Med. Res. Rev. 1998, 3, 149.
5. 5. For review: Thompson, A. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
6. 6. For review: Hermkens, P. H. H.; Ottenheim, H. C. J.; Rees, D. Tetrahedron 1996, 53, 5643.
7. 7. For example: Cheng, S.; Comer, D. D.; Williams, J. P.; Meyers, P.L.; Boger, D. L. J. Am. Chem. Soc. 1996, 118, 2567.
8. 8. For review: Merritt, A. T. Combi. Chem. High Through. Screen. 1998, 1, 51.
9. 9. For example: Han, H.; Janda, K. D. J. Am. Chem. Soc. 1997, 118, 7632.
10. 10. For example: Parlow, J. J.; Naing, W.; South, M. S.; Flynn, D. L. Tetrahedron Lett. 1997, 38, 7959.
11. 11. For review: Mitsunobu, O. Synthesis 1981, 1.
12. 12. For review: Hughes, D. L. Org. React. 1992, 42, 335.
13. 13. For review: Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127.
14. 14. Amos, R. A.; Emblidge, R. W.; Havens, N. J. Org. Chem. 1983, 48, 3598.
15. 15. The polymer-bound triphenylphosphine (∼ 3 mmol triphenylphosphine/g resin) was obtained from Fluka (catalogue no. 93093). Polystyrene is crosslinked with 2% divinylbenzene, diphenylphosphinated.
16. 3)6 14.5, 23.0, 26.3, 29.4, 29.6, 32.1, 45.0, 69.0, 80.0, 108.6, 119.7, 121.1, 126.1, 126.5, 126.7, 129.1, 129.2, 139.3, 154.2, 156.5, 192.4; mp 69 °C.