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Volumn , Issue 10, 2004, Pages 1699-1702

Microwave-assisted Suzuki-Miyaura reactions with an insoluble pyridine-aldoxime Pd-catalyst

Author keywords

Precatalyst; Pyridine aldoxime Pd catalyst; Suzuki miyaura reactions

Indexed keywords

ALDOXIME; ORGANIC SOLVENT; PALLADIUM; PYRIDINE; WATER;

EID: 4143081487     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829546     Document Type: Article
Times cited : (66)

References (30)
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    • Reviews on immobilized precatalysts: (a) Solodenko, W.; Frenzel, T.; Kirschning, A. In Polymeric Materials in Organic Synthesis and Catalysis; Buchmeiser, M. R., Ed.; Wiley-VCH: Weinheim, 2003, 201-240. (b) Clapham, B.; Reger, T. S.; Janda, K. D. Tetrahedron 2001, 57, 4637. (c) Gladysz, J. A. Chem. Rev. 2002, 102, 3215. (d) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
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    • Reviews on immobilized precatalysts: (a) Solodenko, W.; Frenzel, T.; Kirschning, A. In Polymeric Materials in Organic Synthesis and Catalysis; Buchmeiser, M. R., Ed.; Wiley-VCH: Weinheim, 2003, 201-240. (b) Clapham, B.; Reger, T. S.; Janda, K. D. Tetrahedron 2001, 57, 4637. (c) Gladysz, J. A. Chem. Rev. 2002, 102, 3215. (d) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
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    • Reviews on immobilized precatalysts: (a) Solodenko, W.; Frenzel, T.; Kirschning, A. In Polymeric Materials in Organic Synthesis and Catalysis; Buchmeiser, M. R., Ed.; Wiley-VCH: Weinheim, 2003, 201-240. (b) Clapham, B.; Reger, T. S.; Janda, K. D. Tetrahedron 2001, 57, 4637. (c) Gladysz, J. A. Chem. Rev. 2002, 102, 3215. (d) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
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    • 0036810670 scopus 로고    scopus 로고
    • Reviews on immobilized precatalysts: (a) Solodenko, W.; Frenzel, T.; Kirschning, A. In Polymeric Materials in Organic Synthesis and Catalysis; Buchmeiser, M. R., Ed.; Wiley-VCH: Weinheim, 2003, 201-240. (b) Clapham, B.; Reger, T. S.; Janda, K. D. Tetrahedron 2001, 57, 4637. (c) Gladysz, J. A. Chem. Rev. 2002, 102, 3215. (d) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
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    • The Emrys™ Optimizer from Personal Chemistry was used for all experiments described here
    • The Emrys™ Optimizer from Personal Chemistry was used for all experiments described here.
  • 15
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    • The Suzuki-Miyaura reaction (according to Scheme 2) could be repeated at room temperature and was completed within one week to yield the coupling product in 93% isolated yield
    • The Suzuki-Miyaura reaction (according to Scheme 2) could be repeated at room temperature and was completed within one week to yield the coupling product in 93% isolated yield.
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    • Reviews on microwave-assisted synthesis: (a) Kuhnert, N. Angew. Chem. Int. Ed. 2002, 41, 1863. (b) Ferreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199. (c) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95. (d) Kappe, C. O. Curr. Opin. Chem. Biol. 2002, 6, 314. (e) Larhed, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406. (f) Krstenansky, J. F.; Cotterill, I. Curr. Opin. Drug Disc. Dev. 2000, 3, 451.
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    • Reviews on microwave-assisted synthesis: (a) Kuhnert, N. Angew. Chem. Int. Ed. 2002, 41, 1863. (b) Ferreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199. (c) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95. (d) Kappe, C. O. Curr. Opin. Chem. Biol. 2002, 6, 314. (e) Larhed, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406. (f) Krstenansky, J. F.; Cotterill, I. Curr. Opin. Drug Disc. Dev. 2000, 3, 451.
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    • Reviews on microwave-assisted synthesis: (a) Kuhnert, N. Angew. Chem. Int. Ed. 2002, 41, 1863. (b) Ferreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199. (c) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95. (d) Kappe, C. O. Curr. Opin. Chem. Biol. 2002, 6, 314. (e) Larhed, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406. (f) Krstenansky, J. F.; Cotterill, I. Curr. Opin. Drug Disc. Dev. 2000, 3, 451.
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    • Reviews on microwave-assisted synthesis: (a) Kuhnert, N. Angew. Chem. Int. Ed. 2002, 41, 1863. (b) Ferreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199. (c) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95. (d) Kappe, C. O. Curr. Opin. Chem. Biol. 2002, 6, 314. (e) Larhed, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406. (f) Krstenansky, J. F.; Cotterill, I. Curr. Opin. Drug Disc. Dev. 2000, 3, 451.
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    • Reviews on microwave-assisted synthesis: (a) Kuhnert, N. Angew. Chem. Int. Ed. 2002, 41, 1863. (b) Ferreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199. (c) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95. (d) Kappe, C. O. Curr. Opin. Chem. Biol. 2002, 6, 314. (e) Larhed, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406. (f) Krstenansky, J. F.; Cotterill, I. Curr. Opin. Drug Disc. Dev. 2000, 3, 451.
    • (2001) Drug Discovery Today , vol.6 , pp. 406
    • Larhed, M.1    Hallberg, A.2
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    • Reviews on microwave-assisted synthesis: (a) Kuhnert, N. Angew. Chem. Int. Ed. 2002, 41, 1863. (b) Ferreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199. (c) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95. (d) Kappe, C. O. Curr. Opin. Chem. Biol. 2002, 6, 314. (e) Larhed, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406. (f) Krstenansky, J. F.; Cotterill, I. Curr. Opin. Drug Disc. Dev. 2000, 3, 451.
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    • Yields of homo-coupled products were below 5%
    • Yields of homo-coupled products were below 5%.


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