Ionic Liquid Acceleration of Solid-Phase Suzuki-Miyaura Cross-Coupling Reactions

Organic Letters

Volumn 4, Issue 18, 2002, Pages 3071-3073

  Revell, Jefferson D ^a   Ganesan, A ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM TETRAFLUOROBORATE; 1-BUTYL-3-METHYLIMIDAZOLIUM TETRAFLUOROBORATE; 4 IODOPHENOL; 4-IODOPHENOL; BORIC ACID; BORONIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; IODOBENZENE; ION; PALLADIUM; RESIN; SOLVENT;

ARTICLE; CATALYSIS; CHEMISTRY; COMBINATORIAL CHEMISTRY; INDUSTRIAL WASTE; POLLUTION; RECYCLING; STANDARD;

BORATES; BORONIC ACIDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; ENVIRONMENTAL POLLUTION; EQUIPMENT REUSE; IMIDAZOLES; INDUSTRIAL WASTE; IODOBENZENES; IONS; PALLADIUM; RESINS, SYNTHETIC; SOLVENTS;

EID: 0037026549     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0263292     Document Type: Article

References (20)

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2. For some reviews, see: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789. (c) Sheldon, R. Chem. Commun. 2001, 2399-2407. (d) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A 2002, 182, 419-437.
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5. For a recent review, see: Ganesan, A. Drug Discovery Today 2002, 7, 47-55.
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8. For some recent examples, see: (a) Lutz, C.; Bleicher, K. H. Tetrahedron Lett. 2002, 43, 2211-2214. (b) Hanazawa, T.; Wada, T.; Masuda, T.; Okamoto, S.; Sato, F. Org. Lett. 2001, 3, 3975-3977. (c) Barn, D.; Caulfield, W.; Cowley, P.; Dickins, R.; Bakker, W. I.; McGuire, R.; Morphy, J. R.; Rankovic, Z.; Thorn, M. J. Comb. Chem. 2001, 3, 534-541. (d) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (e) Park, C.; Burgess, K. J. Comb. Chem. 2001, 3, 257-266. (f) Pourbaix, C.; Carreaux, F.; Carboni, B. Org. Lett. 2001, 3, 803-805.
9. For some recent examples, see: (a) Lutz, C.; Bleicher, K. H. Tetrahedron Lett. 2002, 43, 2211-2214. (b) Hanazawa, T.; Wada, T.; Masuda, T.; Okamoto, S.; Sato, F. Org. Lett. 2001, 3, 3975-3977. (c) Barn, D.; Caulfield, W.; Cowley, P.; Dickins, R.; Bakker, W. I.; McGuire, R.; Morphy, J. R.; Rankovic, Z.; Thorn, M. J. Comb. Chem. 2001, 3, 534-541. (d) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (e) Park, C.; Burgess, K. J. Comb. Chem. 2001, 3, 257-266. (f) Pourbaix, C.; Carreaux, F.; Carboni, B. Org. Lett. 2001, 3, 803-805.
10. For some recent examples, see: (a) Lutz, C.; Bleicher, K. H. Tetrahedron Lett. 2002, 43, 2211-2214. (b) Hanazawa, T.; Wada, T.; Masuda, T.; Okamoto, S.; Sato, F. Org. Lett. 2001, 3, 3975-3977. (c) Barn, D.; Caulfield, W.; Cowley, P.; Dickins, R.; Bakker, W. I.; McGuire, R.; Morphy, J. R.; Rankovic, Z.; Thorn, M. J. Comb. Chem. 2001, 3, 534-541. (d) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (e) Park, C.; Burgess, K. J. Comb. Chem. 2001, 3, 257-266. (f) Pourbaix, C.; Carreaux, F.; Carboni, B. Org. Lett. 2001, 3, 803-805.
11. For some recent examples, see: (a) Lutz, C.; Bleicher, K. H. Tetrahedron Lett. 2002, 43, 2211-2214. (b) Hanazawa, T.; Wada, T.; Masuda, T.; Okamoto, S.; Sato, F. Org. Lett. 2001, 3, 3975-3977. (c) Barn, D.; Caulfield, W.; Cowley, P.; Dickins, R.; Bakker, W. I.; McGuire, R.; Morphy, J. R.; Rankovic, Z.; Thorn, M. J. Comb. Chem. 2001, 3, 534-541. (d) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (e) Park, C.; Burgess, K. J. Comb. Chem. 2001, 3, 257-266. (f) Pourbaix, C.; Carreaux, F.; Carboni, B. Org. Lett. 2001, 3, 803-805.
12. For some recent examples, see: (a) Lutz, C.; Bleicher, K. H. Tetrahedron Lett. 2002, 43, 2211-2214. (b) Hanazawa, T.; Wada, T.; Masuda, T.; Okamoto, S.; Sato, F. Org. Lett. 2001, 3, 3975-3977. (c) Barn, D.; Caulfield, W.; Cowley, P.; Dickins, R.; Bakker, W. I.; McGuire, R.; Morphy, J. R.; Rankovic, Z.; Thorn, M. J. Comb. Chem. 2001, 3, 534-541. (d) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (e) Park, C.; Burgess, K. J. Comb. Chem. 2001, 3, 257-266. (f) Pourbaix, C.; Carreaux, F.; Carboni, B. Org. Lett. 2001, 3, 803-805.
13. For some recent examples, see: (a) Lutz, C.; Bleicher, K. H. Tetrahedron Lett. 2002, 43, 2211-2214. (b) Hanazawa, T.; Wada, T.; Masuda, T.; Okamoto, S.; Sato, F. Org. Lett. 2001, 3, 3975-3977. (c) Barn, D.; Caulfield, W.; Cowley, P.; Dickins, R.; Bakker, W. I.; McGuire, R.; Morphy, J. R.; Rankovic, Z.; Thorn, M. J. Comb. Chem. 2001, 3, 534-541. (d) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751-4754. (e) Park, C.; Burgess, K. J. Comb. Chem. 2001, 3, 257-266. (f) Pourbaix, C.; Carreaux, F.; Carboni, B. Org. Lett. 2001, 3, 803-805.
14. Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249-1250.
15. -] was purchased from Fluka and used without further purification.
16. Hanessian, S.; Xie, F. Tetrahedron Lett. 1998, 39, 733-736.
17. Recently, ionic liquid-promoted Suzuki reactions were carried out at ambient temperature with the aid of ultrasound: Rajagopal, R.; Jarikote, D. V.; Srinivasan, K. V. Chem. Commun. 2002, 616-617.
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20. 3 (∼500 mg), and the resulting dark-colored mixture was filtered, concentrated, and dried. The crude product was taken up in 15 mL of 1:1 EtOAc/hexanes, adsorbed onto silica (2 g), loaded on a short silica plug (2 g), and eluted. Pure product fractions were combined and concentrated.