Literature DB >> 14870851

Combination of microwave reactions with fluorous separations in the palladium-catalyzed synthesis of aryl sulfides.

Wei Zhang1, Yimin Lu, Christine Hiu-Tung Chen.   

Abstract

Coupling of microwave reactions with fluorous separations can dramatically increase the efficiency of high-speed synthesis. Described in this paper is a fluorous synthesis of aryl sulfides by palladium-catalyzed cross-coupling of aryl perfluoroalkylsulfonates (C8F17O2SOAr) with thiols (RSH) under microwave irradiation. Fluorous solid-phase extractions (F-SPE) are employed for the purification of reaction mixtures. No fluorous solvents are involved in reaction and separation processes. The fluorous synthesis is further extended to the multi-step synthesis of substituted hydantoin and amide scaffolds.

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Year:  2003        PMID: 14870851      PMCID: PMC1894905          DOI: 10.1023/b:modi.0000006825.12186.5f

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  12 in total

1.  Microwave-assisted high-speed chemistry: a new technique in drug discovery.

Authors:  M Larhed; A Hallberg
Journal:  Drug Discov Today       Date:  2001-04-01       Impact factor: 7.851

2.  Carbonminus signCarbon Bond Forming Solid-Phase Reactions.

Authors:  Beth A. Lorsbach; Mark J. Kurth
Journal:  Chem Rev       Date:  1999-06-09       Impact factor: 60.622

Review 3.  The impact of microwave-assisted organic chemistry on drug discovery.

Authors:  Bernard Wathey; Jason Tierney; Pelle Lidström; Jacob Westman
Journal:  Drug Discov Today       Date:  2002-03-15       Impact factor: 7.851

Review 4.  High-speed combinatorial synthesis utilizing microwave irradiation.

Authors:  C Oliver Kappe
Journal:  Curr Opin Chem Biol       Date:  2002-06       Impact factor: 8.822

5.  Tag strategy for separation and recovery.

Authors:  Jun-Ichi Yoshida; Kenichiro Itami
Journal:  Chem Rev       Date:  2002-10       Impact factor: 60.622

Review 6.  Enhancement of combinatorial chemistry by microwave-assisted organic synthesis.

Authors:  Pelle Lidström; Jacob Westman; Anthony Lewis
Journal:  Comb Chem High Throughput Screen       Date:  2002-09       Impact factor: 1.339

7.  Modern separation techniques for the efficient workup in organic synthesis.

Authors:  Carl Christoph Tzschucke; Christian Markert; Willi Bannwarth; Sebastian Roller; André Hebel; Rainer Haag
Journal:  Angew Chem Int Ed Engl       Date:  2002-11-04       Impact factor: 15.336

Review 8.  Microwave-accelerated homogeneous catalysis in organic chemistry.

Authors:  Mats Larhed; Christina Moberg; Anders Hallberg
Journal:  Acc Chem Res       Date:  2002-09       Impact factor: 22.384

9.  Fluorous synthesis of hydantoins and thiohydantoins.

Authors:  Wei Zhang; Yimin Lu
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

10.  Fluorous synthesis of disubstituted pyrimidines.

Authors:  Wei Zhang
Journal:  Org Lett       Date:  2003-04-03       Impact factor: 6.005

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  12 in total

Review 1.  Fluorous synthesis of heterocyclic systems.

Authors:  Wei Zhang
Journal:  Chem Rev       Date:  2004-05       Impact factor: 60.622

Review 2.  Advances in microwave-assisted combinatorial chemistry without polymer-supported reagents.

Authors:  Rafael Martínez-Palou
Journal:  Mol Divers       Date:  2006-08-01       Impact factor: 2.943

3.  Microwave-Enhanced Fluorous Synthesis.

Authors:  Wei Zhang
Journal:  Chim Oggi       Date:  2005

4.  Microwave-assisted synthesis of a 3-aminoimidazo[1,2-a]-pyridine/pyrazine library by fluorous multicomponent reactions and subsequent cross-coupling reactions.

Authors:  Yimin Lu; Wei Zhang
Journal:  QSAR Comb Sci       Date:  2004

5.  Synthetic applications of fluorous solid-phase extraction (F-SPE).

Authors:  Wei Zhang; Dennis P Curran
Journal:  Tetrahedron       Date:  2006-12-18       Impact factor: 2.457

Review 6.  Fluorous tagging strategy for solution-phase synthesis of small molecules, peptides and oligosaccharides.

Authors:  Wei Zhang
Journal:  Curr Opin Drug Discov Devel       Date:  2004-11

7.  Fluorous parallel synthesis of a hydantoin/thiohydantoin library.

Authors:  Yimin Lu; Wei Zhang
Journal:  Mol Divers       Date:  2005       Impact factor: 2.943

8.  A highly efficient microwave-assisted suzuki coupling reaction of aryl perfluorooctylsulfonates with boronic acids.

Authors:  Wei Zhang; Christine Hiu-Tung Chen; Yimin Lu; Tadamichi Nagashima
Journal:  Org Lett       Date:  2004-04-29       Impact factor: 6.005

9.  Microwave-Enhanced High-Speed Fluorous Synthesis.

Authors:  Wei Zhang
Journal:  Top Curr Chem       Date:  2006-08-30

10.  Fluorous Synthesis of Hydantoin-, Piperazinedione-, and Benzodiazepinedione-Fused Tricyclic and Tetracyclic Ring Systems.

Authors:  Wei Zhang; Yimin Lu; Christine Hiu-Tung Chen; Dennis P Curran; Steven Geib
Journal:  European J Org Chem       Date:  2006
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