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Intermolecular hydroamination of vinyl arenes with aryl- and alkylamines: Pd catalysts: a M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 9546;
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Intermolecular hydroamination of vinyl arenes with aryl- and alkylamines: Pd catalysts: a) M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 9546;
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13
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33244484834
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A. M. Johns, M. Utsunomiya, C. D. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 1828, and references therein;
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c) A. M. Johns, M. Utsunomiya, C. D. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 1828, and references therein;
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14
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1542317835
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Ru catalysts: d M. Utsunomiya, J. F. Hartwig, J. Am. Chem. Soc. 2004, 126, 2702;
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Ru catalysts: d) M. Utsunomiya, J. F. Hartwig, J. Am. Chem. Soc. 2004, 126, 2702;
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15
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0038635789
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Rh catalysts: e M. Utsunomiya, R. Kuwano, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 5608;
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Rh catalysts: e) M. Utsunomiya, R. Kuwano, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 5608;
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16
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0141954256
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organolanthanide catalysts: f J. S. Ryu, G. Y. Li, T. J. Marks, J. Am. Chem. Soc. 2003, 125, 12 584;
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organolanthanide catalysts: f) J. S. Ryu, G. Y. Li, T. J. Marks, J. Am. Chem. Soc. 2003, 125, 12 584;
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17
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1242307864
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for other applications of organolanthanides to intramolecular hydroaminations, see reference [1c,d] and references therein; strong bases: g K. Kumar, D. Michalik, I. G. Castro, A. Tillack, A. Zapf, M. Arlt, T. Heinrich, H. Böttcher, M. Beller, Chem. Eur. J. 2004, 10, 746;
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for other applications of organolanthanides to intramolecular hydroaminations, see reference [1c,d] and references therein; strong bases: g) K. Kumar, D. Michalik, I. G. Castro, A. Tillack, A. Zapf, M. Arlt, T. Heinrich, H. Böttcher, M. Beller, Chem. Eur. J. 2004, 10, 746;
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4: h L. T. Kaspar, B. Fingerhut, L. Ackermann, Angew. Chem. 2005, 117, 6126;
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4: h) L. T. Kaspar, B. Fingerhut, L. Ackermann, Angew. Chem. 2005, 117, 6126;
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Angew. Chem. Int. Ed. 2005, 44, 5972;
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Brønsted acids: i L. L. Anderson, J. Arnold, R. G., Bergman, J. Am. Chem. Soc. 2005, 127, 14 542.
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Brønsted acids: i) L. L. Anderson, J. Arnold, R. G., Bergman, J. Am. Chem. Soc. 2005, 127, 14 542.
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21
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33845280868
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Selected examples of other intermolecular hydroaminations: Ir catalysts: a A. L. Casalnuovo, J. C. Calabrese, D. Milstein, J. Am. Chem. Soc. 1988, 110, 6738;
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Selected examples of other intermolecular hydroaminations: Ir catalysts: a) A. L. Casalnuovo, J. C. Calabrese, D. Milstein, J. Am. Chem. Soc. 1988, 110, 6738;
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h) R. Dorta, P. Egli, F. Zürcher, A. Löber, J. Am. Chem. Soc. 1997, 119, 10 857;
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Pd catalysts; c O. Löber, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2001, 123, 4366;
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Pd catalysts; c) O. Löber, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2001, 123, 4366;
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24
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0013219448
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d) T. Minami, H. Okamoto, S. Ikeda, R. Tanaka, F. Ozawa, M. Yoshifuji, Angew. Chem. 2001, 113, 4633;
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Minami, T.1
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0035803739
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Angew. Chem. Int. Ed. 2001, 40, 4501;
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Chem. Int. Ed
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26
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0037051616
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Ni catalysts: e J. Pawlas, Y. Nakao, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 3669;
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Ni catalysts: e) J. Pawlas, Y. Nakao, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 3669;
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27
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33846312234
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Rh catalysts: f B. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579, and references therein;
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Rh catalysts: f) B. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579, and references therein;
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28
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20444470280
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Ru catalysts: g C. S. Yi, S. Y. Yun, Org. Lett. 2005, 7, 2181;
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Ru catalysts: g) C. S. Yi, S. Y. Yun, Org. Lett. 2005, 7, 2181;
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29
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1842429591
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Pt catalysts: h J. J. Brunet, M. Cadena, N. C. Chu, O. Diallo, K. Jacob, E. Mothes, Organometallics 2004, 23, 1264;
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Pt catalysts: h) J. J. Brunet, M. Cadena, N. C. Chu, O. Diallo, K. Jacob, E. Mothes, Organometallics 2004, 23, 1264;
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30
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2342426017
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X. Wang, R. A. Widenhoefer, Organometallics 2004 23, 1649; for other examples, see reviews in reference [1].
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i) X. Wang, R. A. Widenhoefer, Organometallics 2004 23, 1649; for other examples, see reviews in reference [1].
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31
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2442590635
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For related hydrohydrazination, see: a
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For related hydrohydrazination, see: a) J. Waser, E. M. Carreira, J. Am. Chem. Soc. 2004, 126, 5676;
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J. Am. Chem. Soc
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Angew. Chem. Int. Ed. 2004, 43, 4099;
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Chem. Int. Ed
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c) J. Waser, J. C. González-Gómez, H. Nambu, P. Huber, E. M. Carreira, Org. Lett. 2005, 7, 4249.
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Waser, J.1
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Huber, P.4
Carreira, E.M.5
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35
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24744469522
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Use of amide nucleophiles in catalytic intermolecular hydroamination: vinyl arenes: a H. Qian, R. A. Widenhoefer, Org. Lett. 2005, 7, 2635;
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Use of amide nucleophiles in catalytic intermolecular hydroamination: vinyl arenes: a) H. Qian, R. A. Widenhoefer, Org. Lett. 2005, 7, 2635;
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36
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24744468197
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simple olefins: b D. Karshtedt, A. T. Bell, T. D. Tilley, J. Am. Chem. Soc. 2005, 127, 12 640;
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simple olefins: b) D. Karshtedt, A. T. Bell, T. D. Tilley, J. Am. Chem. Soc. 2005, 127, 12 640;
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37
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33244465401
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vinyl arenes and simple olefins: c J. Zhang, C.-G. Yang, C. He, J. Am. Chem. Soc. 2006, 128, 1798;
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vinyl arenes and simple olefins: c) J. Zhang, C.-G. Yang, C. He, J. Am. Chem. Soc. 2006, 128, 1798;
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38
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33746110458
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d) X.-Y. Liu, C.-H. Li, C.-M. Che, Org. Lett. 2006, 8, 2707;
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Org. Lett
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Liu, X.-Y.1
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1,3-dienes: e C. Brouwer, C. He, Angew. Chem. 2006, 118, 1776;
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1,3-dienes: e) C. Brouwer, C. He, Angew. Chem. 2006, 118, 1776;
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40
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Angew. Chem. Int. Ed. 2006, 45, 1744; see also reference [8].
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Angew. Chem. Int. Ed. 2006, 45, 1744; see also reference [8].
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41
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0142214634
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For related intermolecular oxidative amination with carboxamides, carbamates, and sulfonamides, see a
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For related intermolecular oxidative amination with carboxamides, carbamates, and sulfonamides, see a) V. I. Timokhin, N. R. Anastasi, S. S. Stahl, J. Am. Chem. Soc. 2003, 125, 12 996;
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Timokhin, V.I.1
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42
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14844317635
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and references therein
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b) J. L. Brice, J. E. Harang, V. I. Timokhin, N. R. Anastasi, S. S. Stahl, J. Am. Chem. Soc. 2005, 127, 2868, and references therein.
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Stahl, S.S.5
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43
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33749036284
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During the preparation of this manuscript, He and co-workers and Hartwig and co-workers independently reported catalytic intermolecular hydroamination of amides using TfOH as a catalyst; see: a
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During the preparation of this manuscript, He and co-workers and Hartwig and co-workers independently reported catalytic intermolecular hydroamination of amides using TfOH as a catalyst; see: a) Z. Li, J. Zhang, C. Brouwer, C.-G. Yang, N. W. Reich, C. He, Org. Lett. 2006, 8, 4175;
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(2006)
Org. Lett
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Li, Z.1
Zhang, J.2
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Yang, C.-G.4
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He, C.6
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44
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33749000858
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b) D. C. Rosenfeld, S. Shekhar, A. Takemiya, M. Utsunomiya, J. F. Hartwig, Org. Lett. 2006, 8, 4179;
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Org. Lett
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Rosenfeld, D.C.1
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Hartwig, J.F.5
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45
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33750047501
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related reactions promoted by heterogeneous Brønsted acids: c K. Motokura, N. Nakagiri, K. Mori, T. Mizugaki, K. Ebitani, K. Jitsukawa, K. Kaneda, Org. Lett. 2006, 8, 4617.
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related reactions promoted by heterogeneous Brønsted acids: c) K. Motokura, N. Nakagiri, K. Mori, T. Mizugaki, K. Ebitani, K. Jitsukawa, K. Kaneda, Org. Lett. 2006, 8, 4617.
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46
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33747291922
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J. G. Taylor, N. Whittall, K. K. Hu, Org. Lett. 2006, 8, 3561.
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Org. Lett
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Taylor, J.G.1
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47
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0030859171
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4 as a π acid, see also: E. Yoshikawa, V. Gevorgyan, N. Asao, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 6781, and references therein.
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4 as a π acid, see also: E. Yoshikawa, V. Gevorgyan, N. Asao, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 6781, and references therein.
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48
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32244442811
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H. Qin, N. Yamagiwa, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 1611.
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J. Am. Chem. Soc
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Qin, H.1
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49
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3 in organic synthesis, see: H. Gaspard-Iloughmane, C. Le Roux, Eur. J. Org. Chem. 2004, 2517.
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3 in organic synthesis, see: H. Gaspard-Iloughmane, C. Le Roux, Eur. J. Org. Chem. 2004, 2517.
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50
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15044358965
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N-bromosuccinimide-catalyzed hydroamination of vinyl arenes with MeO or MeS substituents: S. K. Talluri, A. Sudalai, Org. Lett. 2005, 7, 855.
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N-bromosuccinimide-catalyzed hydroamination of vinyl arenes with MeO or MeS substituents: S. K. Talluri, A. Sudalai, Org. Lett. 2005, 7, 855.
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51
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33846267806
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Because the melting point of 1.4-dioxane is 11.8°C, DME was used alternatively at 8°C.
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Because the melting point of 1.4-dioxane is 11.8°C, DME was used alternatively at 8°C.
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52
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33846302555
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Although the possibility that TfOH is generated from the Hf(OTf) 4/ [Cu(CH3CN)4]PF6 system cannot be excluded completely, we assume that the results in Scheme 1 support the idea that Hf metal works as an active species at least for styrene 1c. For recently reported Brønsted acid catalyzed intermolecular hydroamination with amides, see reference [7
-
6 system cannot be excluded completely, we assume that the results in Scheme 1 support the idea that Hf metal works as an active species at least for styrene 1c. For recently reported Brønsted acid catalyzed intermolecular hydroamination with amides, see reference [7].
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53
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33846291156
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6 system is not applicable to 4-methoxystyrene owing to competitive self-polymerization.
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6 system is not applicable to 4-methoxystyrene owing to competitive self-polymerization.
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