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2142786872
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note
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We would like to thank Arran Chemical Company for a generous gift of ligand 1a.
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28
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84986366227
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The synthesis of 2a followed a modified procedure by Seebach (see Experimental Section). Betschart, C.; Schmidt, B.; Seebach, D. Helv. Chim. Acta 1988, 71, 1999.
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note
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Ligand screening has shown that N-aryl-1,2-diamines (mono or bis) are poor ligands for the N-arylation of indole.
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30
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2142721146
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note
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While they are not recommended as a first choice, in some cases their use may be easier vis á vis long-term storage than for the free base.
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31
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2142776799
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Massachusetts Institute of Technology. Unpublished results
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Induction periods were observed and are currently being studied in similar amide arylation chemistry: Strieter, E. R.; Buchwald, S. L. Massachusetts Institute of Technology, 2002. Unpublished results.
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(2002)
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Strieter, E.R.1
Buchwald, S.L.2
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note
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CuI (98% purity, purchased from Strem) was of a fine powdered quality.
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33
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2142780491
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note
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Tryptamine (entry 4), melatonin (entry 5), and 5-methoxytryptamine (entry 8) gave a single regioisomer by GC/MS of the crude reaction mixture. However, the reaction employing tryptophol (entry 6) as a substrate gave 7% of the respective bis-arylated byproduct (GC/MS).
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34
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0000157513
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Practical palladium catalysts for C-N and C-O bond formation
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Miyaura, N., Ed.; Springer-Verlag: Berlin
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For reviews on Pd-catalyzed amination, see (a) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, p. 133. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576 (1-2), 125. For an example of a new copper-catalyzed amination method, see (e) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
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Topics in Current Chemistry
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Muci, A.R.1
Buchwald, S.L.2
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35
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0032541260
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For reviews on Pd-catalyzed amination, see (a) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, p. 133. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576 (1-2), 125. For an example of a new copper-catalyzed amination method, see (e) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
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Hartwig, J.F.1
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36
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0001038733
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For reviews on Pd-catalyzed amination, see (a) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, p. 133. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576 (1-2), 125. For an example of a new copper-catalyzed amination method, see (e) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
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Wolfe, J.P.1
Wagaw, S.2
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Buchwald, S.L.4
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37
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0008165462
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For reviews on Pd-catalyzed amination, see (a) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, p. 133. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576 (1-2), 125. For an example of a new copper-catalyzed amination method, see (e) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
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J. Organomet. Chem.
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, Issue.1-2
, pp. 125
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Yang, B.H.1
Buchwald, S.L.2
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38
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0037149057
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For reviews on Pd-catalyzed amination, see (a) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, p. 133. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576 (1-2), 125. For an example of a new copper-catalyzed amination method, see (e) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
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(2002)
Org. Lett.
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Kwong, F.Y.1
Klapars, A.2
Buchwald, S.L.3
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39
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2142672018
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note
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3, DMF, 110 °C (63% conversion).
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40
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2142783027
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note
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Following conditions of Table 5: Reaction of 2-methylindole with 2-bromotoluene gave no conversion. Reaction of 2-methylindole with 2-iodotoluene gave 10% conversion. Reaction of 2-methylindole with 2-bromoanisole gave only 47% conversion.
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41
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0032568384
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For a review on allylic protecting groups and their removal with palladium see Guibe, F. Tetrahedron 1998, 54, 2967.
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(1998)
Tetrahedron
, vol.54
, pp. 2967
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Guibe, F.1
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44
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2142670797
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note
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4 purchased from Alfa Aesar could be ground to a fine powder that provided reproducible results for the several reactions where it was used.
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45
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2142784337
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note
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Dodecane was used in the above reactions as an internal GC standard.
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