Fluorous reagents and scavengers versus solid-supported reagents and scavengers, a reaction rate and kinetic comparison

Molecular Diversity

Volumn 9, Issue 4, 2005, Pages 353-359

  Chen, Christine Hiu Tung ^a   Zhang, Wei ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Fluorous reagents; Fluorous scavengers; Isatoic anhydride; Reaction kinetics; Reaction rate; Solid supported reagents; Solid supported scavengers; Thiol; Triphenylphosphine

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; FLUORINE DERIVATIVE; ISATOIC ANHYDRIDE; KETONE DERIVATIVE; REAGENT; SCAVENGER; THIOL; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; COMPARATIVE STUDY; PRIORITY JOURNAL; SOLID; TIME;

AMINES; BENZYL ALCOHOLS; FLUORINE; INDICATORS AND REAGENTS; KETONES; KINETICS; ORGANOPHOSPHORUS COMPOUNDS; OXAZINES; PIPERAZINES; SULFHYDRYL COMPOUNDS;

EID: 28344442833     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-005-8104-3     Document Type: Article

References (51)

1. Selected reviews on polymer-assisted organic synthesis: a) Hodge, P., Organic synthesis using polymer-supported reagents, catalysts and scavengers in simple laboratory flow systems, Curr. Opin. Chem. Biol., 7 (2003) 362-373.
2. b) Kirschning, A., Monenschein, H. and Wittenberg, R., Functionalized polymers - emerging versatile tools for solution-phase chemistry and automated parallel synthesis, Angew. Chem. Int. Ed., 40 (2001) 650-679.
3. c) Polymeric Scavenger Reagents in Organic Synthesis, Eur. J. Org. Chem., (2001) 1213-21224.
4. d) Thompson, L.A., Recent applications of polymer-supported reagents and scavengers in combinatorial, parallel, or multistep synthesis, Curr. Opin. Chem. Biol., 4 (2000) 324-337.
5. e) 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., Multi-step organic synthesis using solid-supported reagents and scavengers: A new paradigm in chemical library generation, J. Chem. Soc., Perkin Trans. 1, 23 (2000), 3815-4195.
6. f) Booth, R.J. and Hodges, J.C., Solid-supported reagent strategies for rapid purification of combinatorial synthesis products, Acc. Chem. Res., 32 (1999) 18-26.
7. g) Parlow, J.J., Devraj, R.V. and South, M.S., Solution-phase chemical library synthesis using polymer-assisted purification techniques, Curr. Opin. Chem. Biol., 3 (1999) 320-336.
8. h) Flynn, D.L., Devraj, R.V., Naing, W., Parlow, J.J., Weidner, J.J. and Yang, S. Polymer-assisted solution phase (PASP) chemical library synthesis, Med. Chem. Res., 8 (1998) 219-243.
9. Recent reviews on fluorous synthesis: a) Handbook of fluorous chemistry, Gladysz, J.A., Hovath, I. and Curran D.P. (eds), Wiley-VCH, New York, 2004.
10. b) Zhang, W., Fluorous synthesis of heterocyclic systems, Chem. Rev., 104 (2004), 2531-2556.
11. c) Zhang, W., Fluorous technologies for solution-phase high-throughput organic synthesis, Tetrahedron, 59 (2003) 4475-4489.
12. d) Gladysz, J.A. and Curran, D.P., Fluorous chemistry: from biphasic catalysis to a parallel chemical universe and beyond, Tetrahedron, 58 (2002) 3823-3825.
13. e) Curran, D.P., In Stimulating Concepts in Chemistry, Stoddard, F., Reinhoudt, D., Shibasaki, M. (eds.), Wiley-VCH, New York, 2000, pp 25-37.
14. f) Curran, D.P., Strategy-Level separations in organic synthesis: From planning to practice, Angew. Chem., Int. Ed., 37 (1998) 1175-1196.
15. Curran, D.P., Fluorous reverse phase silica gel: A new tool for preparative separations in synthetic organic and organofluorine chemistry, Synlett, (2001) 1488-1496.
16. a) Zhang, W. and Tempest, P., Highly efficient microwave-assisted fluorous Ugi and post-condensation reactions for benzimidazoles and quinoxalinones, Tetrahedron Lett., 45 (2004) 6757-6760.
17. b) Zhang, W., Nagashima, T., Lu, Y. and Chen, C.H.-T., A traceless perfluorooctylsulfonyl tag for deoxygenation of phenols under microwave irradiation, Tetrahedron Lett., 45 (2004) 4611-1613.
18. c) Zhang, W., Chen, C. H.-T., Lu, Y. and Nagashima, T., A Highly efficient microwave-assisted Suzuki coupling reaction of aryl perfluorooctylsulfonates with boronic acids, Org. Lett., 6 (2004) 1473-1476.
19. d) Zhang, W., Lu, Y. and Chen, C.H.-T., Combination of microwave reactions with fluorous separations in the palladium-catalyzed synthesis of arylsuljides, Mol. Diversity, 7 (2003), 199-202.
20. e) Larhed, M., Hoshino, M., Hadida, S., Curran, D.P. and Hallberg, A., Rapid fluorous Stille coupling reactions conducted under microwave irradiation, J. Org. Chem., 62 (1997) 5583-5587.
21. f) Olofsson, K., Kim, S.Y., Larhed, M., Curran, D.P. and Hallberg. A., High-speed, highly fluorous organic reactions, J. Org. Chem., 64 (1999) 4539-4541.
22. a) Linclau, B., Singh, A.K. and Curran, D.P., Organic-fluorous phase switches: A fluorous amine scavenger for purification in solution phase parallel synthesis, J. Org. Chem., 64 (1999) 2835-2842.
23. b) Curran, D.P., Hadida, S., Kim, S.Y. and Luo, Z.Y., Fluorous tin hydrides: A new family of reagents for use and reuse in radical reactions, J. Am. Chem. Soc., 121 (1999) 6607-6615.
24. c) Werner, S. and Curran, D.P., Fluorous dienophiles are powerful diene scavengers in Diels-Alder reactions, Org. Lett., 5 (2003) 3293-3296.
25. a) Lindsley, C.W., Zhao, Z. and Leister, W., Fluorous scavengers in Handbook of fluorous chemistry, Gladysz, J.A., Hovath, I., Curran D.P. (eds.), Wiley-VCH, New York, 2004, pp 236-246.
26. b) Lindsley, C.W., Zhao, Z. and Leister, W., Fluorous-tethered quenching reagents for solution phase parallel synthesis, Tetrahedron Lett., 43 (2002) 4225-4228.
27. c) Lindsley, C.W., Zhou, Z., Leister, W.H. and Strauss. K.A., Fluorous-tethered amine bases for organic and parallel synthesis: Scope and limitations, Tetrahedron Lett., 44 (2003) 3619-3623.
28. a) Zhang, W., Fluorous scavengers for solution-phase synthesis, The Worldwide PharmaChem Directory, 2003, pp. 18-20.
29. b) Zhang, W., Curran, D.P. and Chen, C.H.-T., Use of fluorous silica gel to separate fluorous thiol quenching derivatives in solution-phase parallel synthesis, Tetrahedron, 58 (2002) 3871-3875.
30. c) Zhang, W., Chen, C.H.-T. and Nagashima, T., Fluorous electrophilic scavengers for solution-phase parallel synthesis, Tetrahedron Lett., 44 (2003) 2065-2068.
31. For polymer-supported isatoic anhydride, see Coppola, G.M., A new scavenger resin for amines, Tetrahedron Lett., 39 (1998) 8233-8236.
32. Gladysz, J.A. Ponytails: Structural and electronic considerations in The handbook of fluorous chemistry, Gladysz, J.A., Hovath, I., Curran D.P. (eds), Wiley-VCH, New York, 2004, pp. 41-55.
33. Appel, R. and Halstenberg, M., Organophosphorous reagents in organic synthesis, Cadogan, J.I.G., Ed., Academic, New York, 1979, pp. 387-131.
34. For applications of PS-TPP, see: a) Harrison, C.R., Hodge, P., Hunt, B.J., Khoshdel, E. and Richardson, G., Preparation of alkyl chlorides, acid chlorides, and amides using polymer-supported phosphines and carbon tetrachloride: Mechanism of these reactions, J. Org. Chem., 48 (1983) 3721-3728.
35. b) Caldarelli, M., Habermann, J. and Ley, S.V., Clean five-step synthesis of an array of 1,2,3,4-tetra-substituted pyrroles using polymer-supported reagents, J. Chem. Soc., Perkin Trans., 1, (1999) 107-110.
36. c) Porwanski, S., Kryczka, B. and Marsura, A., A polymer-supported 'one-pot' phosphine imide reaction on cyclodextrins, Tetrahedron Lett., 43 (2002) 8441-8443.
37. For applications of F-TPPs bearing one-, two-, or three-fluorous tags, see: a) Grigg, R. and York, M., Bimetallic catalytic cascade ring closing metathesis - intramolecular Heck reactions using a fluorous biphasic solvent system or a polymer-supported palladium catalyst, Tetrahedron Lett., 41 (2000) 7255-7258.
38. b) Schneider, S. and Bannwarth, W., Repetitive application ofperfluoro-tagged Pd complexes for Stille couplings in a fluorous biphasic system, Angew. Chem. Int. Ed., 39 (2000) 4142-4145.
39. c) Richter, B., de Wolf, E., van Koten, G. and Deelman, B.J., Synthesis and properties of a novel family of fluorous triphenylphosphine derivatives, J. Org. Chem., 65 (2000) 3885-3893.
40. d) Schneider, S. and Bannwarth, W. Application of the fluorous biphase concept to palladium-catalyzed Suzuki couplings, Helv. Chim. Acta., 84 (2001) 735-742.
41. 3 (n = 6, 8, 10), Organometallics, 20 (2001) 3079-3086.
42. f) Dandapani, S. and Curran, D. P. Fluorous Mitsunobu reagents and reactions, Tetrahedron 58 (2002) 3855-3864.
43. g) Parallel fluorous biphasic synthesis of 3H-quinazolin-4-ones by an Aza-Wittig reaction employing perfluoroalkyl-tagged triphenylphosphine, Barthelemy, S., Schneider, S., Bannwarth, W., Tetrahedron Lett., 43 (2002) 807-810.
44. h) Desmaris, L., Percina, N., Cottier, L. and Sinou, D., Conversion of alcohols to bromides using a fluorous phosphine, Tetrahedron Lett., 44 (2003) 7589-7591.
45. Lindsley, C.W., Zhao, Z., Newton, R.C., Leister, W. and Strauss, K.A., A general protocol for solution-phase parallel synthesis, Tetrahedron Lett., 43 (2002) 4467-4470.
46. Selected reviews: a) Walsh, D., Wu, D. and Chang, Y.-T., Understanding the effects of the polymer support on reaction rates and kinetics: Knowledge toward efficient synthetic design, Curr. Opin. Chem. Biol., 7 (2003) 353-361.
47. b) Yan, B., Single-bead analysis in combinatorial chemistry, Curr. Opin. Chem. Biol., 6 (2002) 328-332.
48. c) Rana. S., White, P. and Bradley, M., Influence of resin cross-linking on solid-phase chemistry, J. Comb. Chem., 3 (2001) 9-15.
49. d) Groth, T., Grotli, M. and Meldal, M., Diffusion of reagents in macrobeads, J. Comb. Chem., 3 (2001) 461-168.
50. e) Vaino, A.R. and Janda, K.D., Solid-phase organic synthesis: A critical understanding of the resin, J. Comb. Chem., 2 (2000) 579-596.
51. f) Bing, Y., Monitoring the progress and the yield of solid phase organic reactions directly on resin supports, Acc. Chem. Res., 31 (1998) 621-630.