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Literature DB >> 15101770

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

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

Abstract

[reaction: see text] A new strategy to improve the efficiency of Suzuki coupling reactions is introduced by combining fast microwave reaction with easy fluorous separation. Aryl perfluorooctylsulfonates derived from the corresponding phenols are coupled with aryl boronic acids to form biaryls under general microwave conditions. Both intermediates and products are purified by solid-phase extraction over FluoroFlash silica gel. Application of this tagging strategy to multistep synthesis of biaryl-substituted hydantoin is also described.

Entities: Chemical

Mesh：

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Year: 2004 PMID： 15101770 PMCID： PMC1618883 DOI： 10.1021/ol0496428

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

14 in total

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

2. Synthesis of 4-(5-iodo-3-methylpyrazolyl) phenylsulfonamide and its elaboration to a COX II inhibitor library by solution-phase suzuki coupling using Pd/C as a solid-supported catalyst.

Authors: Michael G Organ; Stanislas Mayer
Journal: J Comb Chem Date: 2003 Mar-Apr

3. Tag strategy for separation and recovery.

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

4. 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

5. Attachment of unreactive amines to the solid support: synthesis of phenyl-substituted anilines, 2-aminopyridines, and 2-aminopyrimidines.

Authors: Shirong Zhu; Shuhao Shi; Samuel W Gerritz; Michael J Sofia
Journal: J Comb Chem Date: 2003 May-Jun

Review 6. 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

7. An assembled complex of palladium and non-cross-linked amphiphilic polymer: a highly active and recyclable catalyst for the Suzuki-Miyaura reaction.

Authors: Yoichi M A Yamada; Koji Takeda; Hideyo Takahashi; Shiro Ikegami
Journal: Org Lett Date: 2002-10-03 Impact factor: 6.005

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

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

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

1. Carbonminus signCarbon Bond Forming Solid-Phase Reactions.

2. Synthesis of 4-(5-iodo-3-methylpyrazolyl) phenylsulfonamide and its elaboration to a COX II inhibitor library by solution-phase suzuki coupling using Pd/C as a solid-supported catalyst.

3. Tag strategy for separation and recovery.

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

5. Attachment of unreactive amines to the solid support: synthesis of phenyl-substituted anilines, 2-aminopyridines, and 2-aminopyrimidines.

Review 6. Microwave-accelerated homogeneous catalysis in organic chemistry.

7. An assembled complex of palladium and non-cross-linked amphiphilic polymer: a highly active and recyclable catalyst for the Suzuki-Miyaura reaction.

8. Metal-catalyzed release of supported boronic acids for C-C bond formation.

9. Suzuki cross-coupling of solid-supported chloropyrimidines with arylboronic acids.

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

Review 1. Advances in microwave-assisted combinatorial chemistry without polymer-supported reagents.

2. Microwave-Enhanced Fluorous Synthesis.

Review 3. Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

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

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

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

7. Plate-to-plate fluorous solid-phase extraction for solution-phase parallel synthesis.

8. Palladium-Catalyzed Buchwald-Hartwig Type Amination of Fluorous Arylsulfonates.

9. Microwave-Enhanced High-Speed Fluorous Synthesis.

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