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Volumn 68, Issue 8, 2003, Pages 3327-3329

Sonogashira coupling of aryl halides catalyzed by palladium on charcoal

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHARCOAL; LEACHING; PALLADIUM; SURFACE REACTIONS;

EID: 0344835674     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034149f     Document Type: Article
Times cited : (194)

References (34)
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    • Pd on charcoal in the Suzuki reaction: (a) Marck, G.; Villiger, A.; Buchecker, R. Tetrahedron Lett. 1994, 35, 3277-3280. (b) Gala, D.; Stamford, A.; Jenkins, J.; Kugelman, M. Org. Process Res. Dev. 1997, 1, 163-164. (c) Ennis, D. S.; McManus, J.; Wood-Kaczmar, W.; Richardson, J.; Smith, G. E.; Carstairs, A. Org. Process Res. Dev. 1999, 3, 248-252. (d) LeBlond, C. R.; Andrews, A. T.; Sun, Y.; Sowa, J. R., Jr. Org. Lett. 2001, 3, 1555-1557. (e) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721-2722.
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    • Pd on charcoal in the Suzuki reaction: (a) Marck, G.; Villiger, A.; Buchecker, R. Tetrahedron Lett. 1994, 35, 3277-3280. (b) Gala, D.; Stamford, A.; Jenkins, J.; Kugelman, M. Org. Process Res. Dev. 1997, 1, 163-164. (c) Ennis, D. S.; McManus, J.; Wood-Kaczmar, W.; Richardson, J.; Smith, G. E.; Carstairs, A. Org. Process Res. Dev. 1999, 3, 248-252. (d) LeBlond, C. R.; Andrews, A. T.; Sun, Y.; Sowa, J. R., Jr. Org. Lett. 2001, 3, 1555-1557. (e) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721-2722.
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    • Pd on charcoal in the Suzuki reaction: (a) Marck, G.; Villiger, A.; Buchecker, R. Tetrahedron Lett. 1994, 35, 3277-3280. (b) Gala, D.; Stamford, A.; Jenkins, J.; Kugelman, M. Org. Process Res. Dev. 1997, 1, 163-164. (c) Ennis, D. S.; McManus, J.; Wood-Kaczmar, W.; Richardson, J.; Smith, G. E.; Carstairs, A. Org. Process Res. Dev. 1999, 3, 248-252. (d) LeBlond, C. R.; Andrews, A. T.; Sun, Y.; Sowa, J. R., Jr. Org. Lett. 2001, 3, 1555-1557. (e) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721-2722.
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    • Other examples of singular Pd/C-catalyzed Sonogashira reactions based on ref 4 are: (a) Potts, K. T.; Horwitz, C. P.; Fessak, A.; Keshavarz-K, M.; Nash, K. E.; Toscano, P. J. J. Am. Chem. Soc. 1993, 115, 10444-10445. (b) Bleicher, L.; Cosford, N. D. P. Synlett 1995, 1115-1116. (c) Cosford, N. D. P. et al. J. Med. Chem. 1996, 39, 3235-3237. (d) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109-1118. (e) Felpin, F.-X.; Vo-Thanh, G.; Villiéras, J.; Lebreton, J. Tetrahedron: Asymmetry 2001, 12, 1121-1124. (f) Bates, R. W.; Boonsombat, J. J. Chem. Soc., Perkin Trans. 1 2001, 654-657. (g) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118-1122. (h) Mori, Y.; Seki, M. J. Org. Chem. 2003, 68, 1571-1574.
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    • Other examples of singular Pd/C-catalyzed Sonogashira reactions based on ref 4 are: (a) Potts, K. T.; Horwitz, C. P.; Fessak, A.; Keshavarz-K, M.; Nash, K. E.; Toscano, P. J. J. Am. Chem. Soc. 1993, 115, 10444-10445. (b) Bleicher, L.; Cosford, N. D. P. Synlett 1995, 1115-1116. (c) Cosford, N. D. P. et al. J. Med. Chem. 1996, 39, 3235-3237. (d) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109-1118. (e) Felpin, F.-X.; Vo-Thanh, G.; Villiéras, J.; Lebreton, J. Tetrahedron: Asymmetry 2001, 12, 1121-1124. (f) Bates, R. W.; Boonsombat, J. J. Chem. Soc., Perkin Trans. 1 2001, 654-657. (g) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118-1122. (h) Mori, Y.; Seki, M. J. Org. Chem. 2003, 68, 1571-1574.
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    • Bleicher, L.1    Cosford, N.D.P.2
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    • 0029784854 scopus 로고    scopus 로고
    • Other examples of singular Pd/C-catalyzed Sonogashira reactions based on ref 4 are: (a) Potts, K. T.; Horwitz, C. P.; Fessak, A.; Keshavarz-K, M.; Nash, K. E.; Toscano, P. J. J. Am. Chem. Soc. 1993, 115, 10444-10445. (b) Bleicher, L.; Cosford, N. D. P. Synlett 1995, 1115-1116. (c) Cosford, N. D. P. et al. J. Med. Chem. 1996, 39, 3235-3237. (d) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109-1118. (e) Felpin, F.-X.; Vo-Thanh, G.; Villiéras, J.; Lebreton, J. Tetrahedron: Asymmetry 2001, 12, 1121-1124. (f) Bates, R. W.; Boonsombat, J. J. Chem. Soc., Perkin Trans. 1 2001, 654-657. (g) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118-1122. (h) Mori, Y.; Seki, M. J. Org. Chem. 2003, 68, 1571-1574.
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    • Cosford, N.D.P.1
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    • 0032549047 scopus 로고    scopus 로고
    • Other examples of singular Pd/C-catalyzed Sonogashira reactions based on ref 4 are: (a) Potts, K. T.; Horwitz, C. P.; Fessak, A.; Keshavarz-K, M.; Nash, K. E.; Toscano, P. J. J. Am. Chem. Soc. 1993, 115, 10444-10445. (b) Bleicher, L.; Cosford, N. D. P. Synlett 1995, 1115-1116. (c) Cosford, N. D. P. et al. J. Med. Chem. 1996, 39, 3235-3237. (d) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109-1118. (e) Felpin, F.-X.; Vo-Thanh, G.; Villiéras, J.; Lebreton, J. Tetrahedron: Asymmetry 2001, 12, 1121-1124. (f) Bates, R. W.; Boonsombat, J. J. Chem. Soc., Perkin Trans. 1 2001, 654-657. (g) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118-1122. (h) Mori, Y.; Seki, M. J. Org. Chem. 2003, 68, 1571-1574.
    • (1998) J. Org. Chem. , vol.63 , pp. 1109-1118
    • Bleicher, L.S.1    Cosford, N.D.P.2    Herbaut, A.3    McCallum, J.S.4    McDonald, I.A.5
  • 21
    • 0035926424 scopus 로고    scopus 로고
    • Other examples of singular Pd/C-catalyzed Sonogashira reactions based on ref 4 are: (a) Potts, K. T.; Horwitz, C. P.; Fessak, A.; Keshavarz-K, M.; Nash, K. E.; Toscano, P. J. J. Am. Chem. Soc. 1993, 115, 10444-10445. (b) Bleicher, L.; Cosford, N. D. P. Synlett 1995, 1115-1116. (c) Cosford, N. D. P. et al. J. Med. Chem. 1996, 39, 3235-3237. (d) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109-1118. (e) Felpin, F.-X.; Vo-Thanh, G.; Villiéras, J.; Lebreton, J. Tetrahedron: Asymmetry 2001, 12, 1121-1124. (f) Bates, R. W.; Boonsombat, J. J. Chem. Soc., Perkin Trans. 1 2001, 654-657. (g) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118-1122. (h) Mori, Y.; Seki, M. J. Org. Chem. 2003, 68, 1571-1574.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 1121-1124
    • Felpin, F.-X.1    Vo-Thanh, G.2    Villiéras, J.3    Lebreton, J.4
  • 22
    • 0034991922 scopus 로고    scopus 로고
    • Other examples of singular Pd/C-catalyzed Sonogashira reactions based on ref 4 are: (a) Potts, K. T.; Horwitz, C. P.; Fessak, A.; Keshavarz-K, M.; Nash, K. E.; Toscano, P. J. J. Am. Chem. Soc. 1993, 115, 10444-10445. (b) Bleicher, L.; Cosford, N. D. P. Synlett 1995, 1115-1116. (c) Cosford, N. D. P. et al. J. Med. Chem. 1996, 39, 3235-3237. (d) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109-1118. (e) Felpin, F.-X.; Vo-Thanh, G.; Villiéras, J.; Lebreton, J. Tetrahedron: Asymmetry 2001, 12, 1121-1124. (f) Bates, R. W.; Boonsombat, J. J. Chem. Soc., Perkin Trans. 1 2001, 654-657. (g) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118-1122. (h) Mori, Y.; Seki, M. J. Org. Chem. 2003, 68, 1571-1574.
    • (2001) J. Chem. Soc., Perkin Trans. 1 , pp. 654-657
    • Bates, R.W.1    Boonsombat, J.2
  • 23
    • 0036062734 scopus 로고    scopus 로고
    • Other examples of singular Pd/C-catalyzed Sonogashira reactions based on ref 4 are: (a) Potts, K. T.; Horwitz, C. P.; Fessak, A.; Keshavarz-K, M.; Nash, K. E.; Toscano, P. J. J. Am. Chem. Soc. 1993, 115, 10444-10445. (b) Bleicher, L.; Cosford, N. D. P. Synlett 1995, 1115-1116. (c) Cosford, N. D. P. et al. J. Med. Chem. 1996, 39, 3235-3237. (d) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109-1118. (e) Felpin, F.-X.; Vo-Thanh, G.; Villiéras, J.; Lebreton, J. Tetrahedron: Asymmetry 2001, 12, 1121-1124. (f) Bates, R. W.; Boonsombat, J. J. Chem. Soc., Perkin Trans. 1 2001, 654-657. (g) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118-1122. (h) Mori, Y.; Seki, M. J. Org. Chem. 2003, 68, 1571-1574.
    • (2002) Synlett , pp. 1118-1122
    • Heidenreich, R.G.1    Köhler, K.2    Krauter, J.G.E.3    Pietsch, J.4
  • 24
    • 0037458799 scopus 로고    scopus 로고
    • Other examples of singular Pd/C-catalyzed Sonogashira reactions based on ref 4 are: (a) Potts, K. T.; Horwitz, C. P.; Fessak, A.; Keshavarz-K, M.; Nash, K. E.; Toscano, P. J. J. Am. Chem. Soc. 1993, 115, 10444-10445. (b) Bleicher, L.; Cosford, N. D. P. Synlett 1995, 1115-1116. (c) Cosford, N. D. P. et al. J. Med. Chem. 1996, 39, 3235-3237. (d) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109-1118. (e) Felpin, F.-X.; Vo-Thanh, G.; Villiéras, J.; Lebreton, J. Tetrahedron: Asymmetry 2001, 12, 1121-1124. (f) Bates, R. W.; Boonsombat, J. J. Chem. Soc., Perkin Trans. 1 2001, 654-657. (g) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118-1122. (h) Mori, Y.; Seki, M. J. Org. Chem. 2003, 68, 1571-1574.
    • (2003) J. Org. Chem. , vol.68 , pp. 1571-1574
    • Mori, Y.1    Seki, M.2
  • 26
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    • note
    • Reagents were selected to provide a representative example both in terms of reactivity and utility. Although aromatic iodides react more readily under the applied conditions, aryl bromides are available in far greater numbers and their use is more economical.
  • 27
    • 0344387459 scopus 로고    scopus 로고
    • note
    • Preliminary screening of common phosphorous-based ligands showed that the catalytic system containing triphenylphosphine is not inferior in terms of activity to phosphites, dppe, dppp, dppb, or dppf.
  • 28
    • 0345250362 scopus 로고    scopus 로고
    • note
    • In slower reactions, the competing copper-catalyzed dimerization of the alkyne consumes the reagent before the completion of the Sonogashira coupling.
  • 29
    • 0344387458 scopus 로고    scopus 로고
    • note
    • In certain cases, the reactions were also repeated on a 100 mmol scale and the products were isolated in similar yield using distillation.
  • 30
    • 0344819159 scopus 로고    scopus 로고
    • note
    • For details, see Supporting Information.
  • 31
    • 0037006237 scopus 로고    scopus 로고
    • Recent results suggest that the amount of palladium in solution might further be reduced by the addition of sodium formate at the end of the process. For details, see: Köhler, K.; Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J. Chem. Eur. J. 2002, 8, 622-631.
    • (2002) Chem. Eur. J. , vol.8 , pp. 622-631
    • Köhler, K.1    Heidenreich, R.G.2    Krauter, J.G.E.3    Pietsch, J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.