A bird's eye view of fluorous reaction and separation techniques

Actualite Chimique

Volumn , Issue 4-5, 2003, Pages 67-71

  Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Biphasic and triphasic reactions; Fluorous phase; Mitsunobu reaction; Strategic separation

Indexed keywords

FLUORINE; REAGENT; SILICON DIOXIDE;

CATALYST; CHEMICAL REACTION; CHEMISTRY; CHROMATOGRAPHY; CRYSTALLIZATION; DISTILLATION; ENANTIOMER; ENANTIOSELECTIVITY; LIQUID LIQUID EXTRACTION; MOLECULAR DYNAMICS; REACTION ANALYSIS; RELIABILITY; REVIEW; SEPARATION TECHNIQUE; SOLID PHASE EXTRACTION; SYNTHESIS; TECHNIQUE; TEMPERATURE;

EID: 0038122843     PISSN: 01519093     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (29)

1. Curran D.P., Strategy-level separations in organic synthesis: from planning to practice, Angew. Chem. Int. Ed. Eng., 1998, 37, p. 1175.
2. a) Gladysz J.A., Curran D.P., Introduction - fluorous chemistry: from biphasic catalysis to a parallel chemical universe and beyond, Tetrahedron, 2002, 58, p. 3823;
3. b) See the Tetrahedorn-Symposium-inPrint that follows this introduction.
4. Curran D.P., Fluorous techniques for the synthesis of organic molecules: a unified strategy for reaction and separation, Stimulating concepts in chemistry, Wiley-VCH, New York, 2000, p. 25.
5. a) Barthel-Rosa L.P., Gladysz J.A., Chemistry in fluorous media: a user's guide to practical considerations in the application of fluorous catalysts and reagents, Coord. Chem. Rev., 1999, 192, p. 587;
6. b) Curran D.P., Hadida S., Studer A., He M., Kim S.-Y. et al., Experimental techniques in fluorous synthesis: a user's guide, Combinatorial chemistry: a practical approach, Oxford Univ. Press, Oxford, 2001, p. 327.
7. Curran D.P., Fluorous reverse phase silica gel. A new tool for preparative separations in synthetic organic and organofluorine chemistry, Synlett, 2001, p. 1488.
8. a) Horvath I.T., Rabai J., Facile catalyst separation without water: fluorous biphase hydroformylation of olefins, Science, 1994, 266, p. 72;
9. b) Horvath I.T., Fluorous biphase chemistry, Acc. Chem. Res., 1998, 31, p. 641;
10. c) de Wolf E., van Koten G., Deelman B.J., Fluorous phase separation techniques in catalysis, Chem. Soc. Rev., 1999, 28, p. 37;
11. d) Cavazzini M., Montanari F., Pozzi G., Quici S., Perfluorocarbon-soluble catalysts and reagents and the application of fbs (fluorous biphase system) to organic synthesis, J. Fluorine Chem., 1999, 94, p. 183;
12. e) Fish R.H., Fluorous biphasic catalysis: a new paradigm for the separation of homogeneous catalysts from their reaction substrates and products, Chem. Eur. J., 1999, 5, p. 1677;
13. f) Hope E.G., Stuart A.M., Fluorous biphase catalysis, J. Fluorine Chem., 1999, 100, p. 75-83;
14. g) Gladysz J.A., Recoverable catalysts. Ultimate goals, criteria of evaluation, and the green chemistry interface, Pure Appl Chem., 2001, 73, p. 1319.
15. Wende M., Meier R., Gladysz J.A., Fluorous catalysis without fluorous solvents: a friendlier catalyst recovery/recycling protocol based upon thermomorphic properties and liquid/solid phase separation, J. Am. Chem. Soc., 2001, 123, p. 11490.
16. Nakamura H., Linclau B., Curran D.P., Fluorous triphasic reactions: Transportative deprotection of fluorous silyl ethers with concomitant purification, J. Am. Chem. Soc., 2001, 123, p. 10119.
17. Luo Z.Y., Swaleh S.M., Theil F., Curran D.P., Resolution of 1-(2-naphthyl)ethanol by a combination of an enzyme-catalyzed kinetic resolution with a fluorous triphasic separative reaction, Org. Lett., 2002, 4, p. 2585.
18. a) Curran D.P., Luo Z.Y., Fluorous synthesis with fewer fluorines (light fluorous synthesis): separation of tagged from untagged products by solid-phase extraction with fluorous reverse-phase silica gel, J. Am. Chem. Soc., 1999, 121, p. 9069;
19. b) Zhang Q., Luo Z., Curran D.P., Separation of « light fluorous » reagents and catalysts by fluorous solidphase extraction: synthesis and study of a family of triarylphosphines bearing linear and branched fluorous tags, J. Org. Chem., 2000, 65, p. 8866.
20. a) Lindsley C.W., Zhao Z., Leister W.H., Fluorous-tethered quenching reagents for solution phase parallel synthesis, Tetrahedron Lett., 2002, 43, p. 4225;
21. b) Zhang W., Curran D.P., Chen C.H.T., Use of fluorous silica gel to separate fluorous thiol quenching derivatives in solution-phase parallel synthesis, Tetrahedron, 2002, 58, p. 3871.
22. Zhang W., Chen C.H.-T., Nagashima T., Fluorous electrophilic scavengers for solution phase parallel synthesis, Tetrahedron Lett., 2003, 44, p. 2065.
23. a) Luo Z.Y., Zhang Q.S., Oderaotoshi Y., Curran D.P., Fluorous mixture synthesis: a fluorous-tagging strategy for the synthesis and separation of mixtures of organic compounds, Science, 2001, 291, p. 1766;
24. b) Curran D.P., Oderaotoshi Y., Thiol additions to acrylates by fluorous mixture synthesis: relative control of elution order in demixing by the fluorous tag and the thiol substituent, Tetrahedron, 2001, 57, p. 5243.
25. Zhang Q.S., Rivkin A., Curran D.P., Quasiracemic synthesis: concepts and implementation with a fluorous tagging strategy to make both enantiomers of pyridovericin and mappicine, J. Am. Chem. Soc., 2002, 124, p. 5774.
26. Curran D.P., Furukawa T., Simultaneous preparation of four truncated analogues of discodermolide by fluorous mixture synthesis, Org. Lett., 2002, 4, p. 2233.
27. Zhang W., Chen C.H.-T., Luo Z., Curran D.P., Solution-phase preparation of a 560-compound library of individually pure mappicine analogs by fluorous mixture synthesis, J. Am. Chem. Soc., 2002, 124, p. 10443.
28. Fluorous Technologies, Inc., UPARC, 970 William Pitt Way, Harmarville, PA, 15238 USA (www.fluorous.com). DPC is the Founder and Chief Scientific Advisor and holds an equity interest in FTI.
29. I am indebted to my coworkers at the University of Pittsburgh and to the scientists at Fluorous Technologies, Inc for their many experimental and intellectual contributions. Some of their names are mentioned in the above references. I thank the National Institutes of Health, Merck and Bayer for support.