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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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0001336237
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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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Potts, K.T.1
Horwitz, C.P.2
Fessak, A.3
Keshavarz-K, M.4
Nash, K.E.5
Toscano, P.J.6
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18
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4544313702
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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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Synlett
, pp. 1115-1116
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Bleicher, L.1
Cosford, N.D.P.2
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19
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0029784854
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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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, vol.39
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Cosford, N.D.P.1
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20
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0032549047
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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.S.1
Cosford, N.D.P.2
Herbaut, A.3
McCallum, J.S.4
McDonald, I.A.5
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21
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0035926424
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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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Tetrahedron: Asymmetry
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Felpin, F.-X.1
Vo-Thanh, G.2
Villiéras, J.3
Lebreton, J.4
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22
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0034991922
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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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J. Chem. Soc., Perkin Trans. 1
, pp. 654-657
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Bates, R.W.1
Boonsombat, J.2
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23
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0036062734
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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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Synlett
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Heidenreich, R.G.1
Köhler, K.2
Krauter, J.G.E.3
Pietsch, J.4
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24
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0037458799
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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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Mori, Y.1
Seki, M.2
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25
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0034235216
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For a solvent-free Sonogashira reaction catalyzed by Pd on alumina, see: Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Tetrahedron Lett. 2000, 41, 5151-5154.
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Kabalka, G.W.1
Wang, L.2
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Pagni, R.M.4
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26
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0344819160
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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.
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27
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0344387459
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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.
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28
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0345250362
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note
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In slower reactions, the competing copper-catalyzed dimerization of the alkyne consumes the reagent before the completion of the Sonogashira coupling.
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29
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0344387458
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note
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In certain cases, the reactions were also repeated on a 100 mmol scale and the products were isolated in similar yield using distillation.
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30
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0344819159
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note
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For details, see Supporting Information.
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31
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0037006237
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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.
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Köhler, K.1
Heidenreich, R.G.2
Krauter, J.G.E.3
Pietsch, J.4
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