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

Author:

Chen Christine Hiu-Tung,Zhang Wei

Publisher

Springer Science and Business Media LLC

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Drug Discovery,Molecular Biology,General Medicine,Information Systems,Catalysis

Reference14 articles.

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. 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. c) Polymeric Scavenger Reagents in Organic Synthesis, Eur. J. Org. Chem., (2001) 1213–21224. 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. 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. 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. 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. 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.

2. 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. b) Zhang, W., Fluorous synthesis of heterocyclic systems, Chem. Rev., 104 (2004), 2531–2556. c) Zhang, W., Fluorous technologies for solution-phase high-throughput organic synthesis, Tetrahedron, 59 (2003) 4475–4489. 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. e) Curran, D.P., In Stimulating Concepts in Chemistry, Stoddard, F., Reinhoudt, D., Shibasaki, M. (eds.), Wiley-VCH, New York, 2000, pp 25–37. f) Curran, D.P., Strategy-Level separations in organic synthesis: From planning to practice, Angew. Chem., Int. Ed., 37(1998) 1175–1196.

3. Curran, D.P., Fluorous reverse phase silica gel: A new tool for preparative separations in synthetic organic and organofluorine chemistry, Synlett, (2001) 1488–1496.

4. 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. 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) 4611–4613. 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. 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. 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. 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.

5. 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. 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. c) Werner, S. and Curran, D.P., Fluorous dienophiles are powerful diene scavengers in Diels-Alder reactions, Org. Lett., 5 (2003) 3293–3296.

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