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a) J. March, Advanced Organic Chemistry, 4th ed., Wiley, New York, 1992, chap. 13;
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53549095390
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This reaction was first reported in a catalytic version in 1986: N. V. Kondratenko, A. Kolomeitsev, V. O. Mogilevskaya, N. M. Varlamova, L. M. Yagupol'skii, Zh. Org. Khim. 1986, 8, 1721-1729
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This reaction was first reported in a catalytic version in 1986: N. V. Kondratenko, A. Kolomeitsev, V. O. Mogilevskaya, N. M. Varlamova, L. M. Yagupol'skii, Zh. Org. Khim. 1986, 8, 1721-1729
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For a review, see
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For a review, see: B. Schlummer, U. Scholz, Adv. Synth. Catal. 2004, 346, 1599-1626.
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For a general discussion, see:, 3rd ed, Eds, P. Krogsgaard-Larsen, T. Liljefors, U. Madsen, Taylor and Francis, London, UK, chap. 11
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For a general discussion, see: K. P. Bøgesø, B. Bang-Andersen in Textbook of Drug Design and Discovery, 3rd ed. (Eds.: P. Krogsgaard-Larsen, T. Liljefors, U. Madsen), Taylor and Francis, London, UK, 2002, chap. 11.
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Abbreviations: bmim, n-butylmethyl imidazolium; binap, 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl; davephos, 2-dicyclohexylphosphanyl-2′-(N,N-dimethylamino)biphenyl; dba, dibenzylidine acetone; dpephos, bis(2-diphenylphosphanyl)-ether; dppf, 1,1′-bis(diphenylphosphanyl)ferrocene; xantphos, 4,5- bis(diphenylphosphanyl)-9,9-dimethylxanthene; x-phos, 2-dicyclohexylphosphanyl- 2′,4′-6′-triisopropyl-1,1′-biphenyl
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Abbreviations: bmim = (n-butyl)methyl imidazolium; binap = 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl; davephos = 2-dicyclohexylphosphanyl-2′-(N,N-dimethylamino)biphenyl; dba = dibenzylidine acetone; dpephos = bis(2-diphenylphosphanyl)-ether; dppf = 1,1′-bis(diphenylphosphanyl)ferrocene; xantphos = 4,5- bis(diphenylphosphanyl)-9,9-dimethylxanthene; x-phos = 2-dicyclohexylphosphanyl- 2′,4′-6′-triisopropyl-1,1′-biphenyl.
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The reagents had to be mixed immediately before starting the reactions to avoid catalyst deactivation. Therefore, the classic oil bath conditions were more practical for ligand screening experiments see the Supporting Information for details, All chemicals were weighed out in air without precautions to exclude air from the reaction mixture
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The reagents had to be mixed immediately before starting the reactions to avoid catalyst deactivation. Therefore, the classic oil bath conditions were more practical for ligand screening experiments (see the Supporting Information for details). All chemicals were weighed out in air without precautions to exclude air from the reaction mixture.
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5% of 3-methylindole is formed under these reaction conditions. We have optimized this serendipitous finding to a one-flask approach to 3-substituted indoles. T. Jensen, H. Pedersen, B. Bang-Andersen, R. Madsen, M. Jørgensen, Angew. Chem. 2008, 120, 902-904;
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5% of 3-methylindole is formed under these reaction conditions. We have optimized this serendipitous finding to a one-flask approach to 3-substituted indoles. T. Jensen, H. Pedersen, B. Bang-Andersen, R. Madsen, M. Jørgensen, Angew. Chem. 2008, 120, 902-904;
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No amination products formed with 4-(trifluoromethyl)aniline, 4-amino-benzoic acid ethyl ester, or 4-(dimethylamino)aniline
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No amination products formed with 4-(trifluoromethyl)aniline, 4-amino-benzoic acid ethyl ester, or 4-(dimethylamino)aniline.
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