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See for instance: a
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See for instance: (a) Krolski, M. E.; Renaldo, A. F.; Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1988, 53, 1170-1176.
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8
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4444378913
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(b) Torisu, K.; Kobayashi, K.; Iwahashi, M.; Nakai, Y.; Onoda, T.; Nagase, T.; Sugimoto, I.; Okada, Y.; Matsumoto, R.; Nanbu, F.; Ohuchida, S.; Nakai, H.; Toda, M. Biorg. Med. Chem. Lett. 2004, 14, 4891-4895.
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Nanbu, F.10
Ohuchida, S.11
Nakai, H.12
Toda, M.13
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9
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34447326317
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Functionalization at the 1-, 2-, and 3-positions of the indole ring can be effected easily by conventional methods: Sundberg, R. J. Indoles; Academic Press, London, 1996.
-
Functionalization at the 1-, 2-, and 3-positions of the indole ring can be effected easily by conventional methods: Sundberg, R. J. Indoles; Academic Press, London, 1996.
-
-
-
-
10
-
-
34447322695
-
-
Although 4-hydroxyindole is commercially available, it is quite expensive to be used as starting material in multigram preparations
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Although 4-hydroxyindole is commercially available, it is quite expensive to be used as starting material in multigram preparations.
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11
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0030816416
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(a) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511.
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Kondo, Y.1
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14
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34447305631
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4-Alkoxy-3-formylindoles have been prepared by a one-pot thallation-iodination-alkoxylation reaction sequence from 3-formylindole; see Somei, M.; Yamada, F.; Kunimoto, M.; Kaneko, C. Heterocycles 1984, 22, 797-801.
-
4-Alkoxy-3-formylindoles have been prepared by a one-pot thallation-iodination-alkoxylation reaction sequence from 3-formylindole; see Somei, M.; Yamada, F.; Kunimoto, M.; Kaneko, C. Heterocycles 1984, 22, 797-801.
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16
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37049090963
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(b) Bartoli, G.; Bosco, M.; Dalpozzo, R.; Palmieri, G.; Marcantoni, E. J. Chem. Soc., Perkin Trans. 1 1991, 2757-2761.
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19
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34447343472
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We have optimized the conditions for the ortho-lithiation of 1a by using LDA instead of our initially reported conditions s-BuLi/TMEDA
-
We have optimized the conditions for the ortho-lithiation of 1a by using LDA instead of our initially reported conditions (s-BuLi/TMEDA).
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-
-
-
20
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34447335488
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The protection of the hydroxy group of 2,3-dihalophenols turns out to be necessary because coupling of 3-halo-2-iodophenols with terminal alkynes under copper-palladium-catalyzed conditions afforded benzo[b]-furan derivatives. See ref 10
-
The protection of the hydroxy group of 2,3-dihalophenols turns out to be necessary because coupling of 3-halo-2-iodophenols with terminal alkynes under copper-palladium-catalyzed conditions afforded benzo[b]-furan derivatives. See ref 10.
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21
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0033553109
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Developed by Kondo and Uchiyama for the chemoselective deprotonative zincation of functionalized aromatic compounds: (a) Kondo, Y, Shilai, M, Uchiyama, M, Sakamoto, T. J. Am. Chem. Soc. 1999, 121, 3539-3540
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Developed by Kondo and Uchiyama for the chemoselective deprotonative zincation of functionalized aromatic compounds: (a) Kondo, Y.; Shilai, M.; Uchiyama, M.; Sakamoto, T. J. Am. Chem. Soc. 1999, 121, 3539-3540.
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22
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For a review, see
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(a) For a review, see: Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632-2657.
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24
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Buchwald and Gelman have indeed found that CuI has a deleterious effect on Sonogashira couplings: Gelman, D.; Buchwald, S. L. Angew. Chem., Int. Ed. 2003, 42, 5993-5996.
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(b) Buchwald and Gelman have indeed found that CuI has a deleterious effect on Sonogashira couplings: Gelman, D.; Buchwald, S. L. Angew. Chem., Int. Ed. 2003, 42, 5993-5996.
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25
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For selected papers: (a) Mori, A.; Kawashima, J.; Shimada, T.; Suguro, M.; Hirabayashi, K.; Nishihara, Y. Org. Lett. 2000, 2, 2935-2937.
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(b) Cheng, J.; Sun, Y.; Wang, F.; Guo, M.; Xu, J.-H.; Pan, Y.; Zhang, Z. J. Org. Chem. 2004, 69, 5428-5432.
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34447300074
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We have observed that the reaction of 3-bromo-2-iodoanisole 3e with phenylacetylene (2 equiv) gave rise to a small amount of 2,3-bis(phenylethynyl)anisole. Formation of this side product could be inhibited by using only a slight excess of the alkyne 1.2 equiv
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We have observed that the reaction of 3-bromo-2-iodoanisole 3e with phenylacetylene (2 equiv) gave rise to a small amount of 2,3-bis(phenylethynyl)anisole. Formation of this side product could be inhibited by using only a slight excess of the alkyne (1.2 equiv).
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An alternative approach consisting of a hydroamination and a subsequent intramolecular Pd-catalyzed amination reaction has also been reported: Siebeneicher, H.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 2003, 42, 3042-3044.
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41
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3. However, when we tried this one-pot approach using 3b and phenylacetylene as starting materials, the reaction did not work, probably due to the presence of the Cu(I) salt, which favours the oxidative homocoupling of the alkyne.
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3. However, when we tried this one-pot approach using 3b and phenylacetylene as starting materials, the reaction did not work, probably due to the presence of the Cu(I) salt, which favours the oxidative homocoupling of the alkyne.
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