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a) For a review of additions of amines to alkenes, see: Gase, M. B.; Latties, A.; Perie, J. J. Tetrahedron 1983, 339, 703.
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c) For a review of addition of amines to alkynes, see: Jager, V.; Viehe, H. G. Hoben-wel, Methoden der Organischen Chemie, ' Thieme verlag: Stuttgart, Germany, 1977; vol 5/2a, pp 713.
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Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford. U.K., 1982; Vol. 8, pp 892-895.
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Trost, B.M.1
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9
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0029902948
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and references therein
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a) Organolanthanide-Catalyzed Intramolecular hydroamination: Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295-9306, and references therein.
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and references therein
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b) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 113, 6019, and references therein.
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Besson, L.; Gore, J.; Cazes, B. Tetrahedron Lett. 1995, 36, 3857, and references therein.
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a) Rawal, V. H.; Jones, R. J.; Cava, M. P. J. Org. Chem. 1987, 52, 19-28.
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15
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0342431601
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note
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In tosyl amine cases, when phenylallene : amine ratio was 1:1, isolated yield for 4a and 3j were 62% and 37% respectively and when allene : amine ratio was 2:1, isolated yield for 4a and 3j were 61% and 24% respectively.With allenes 1b and 1f, 1:1 ratio was used.
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16
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0003463148
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T. W. Greene and P. G. M. Wuts. John Wiley & Sons, Inc.
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Protective groups in Organic Synthesis, 2nd Ed.; T. W. Greene and P. G. M. Wuts. John Wiley & Sons, Inc., 1991, pp 379.
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Protective Groups in Organic Synthesis, 2nd Ed.
, pp. 379
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17
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0343301190
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3 and dppf was employed 3a was obtained in lower yield (51%)
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3 and dppf was employed 3a was obtained in lower yield (51%).
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18
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0001687461
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a) Zudin, V. N.; Chikov, V. D.; Nekipelov, V. M.; Likhholov, V. A.; Yermakov, Y. I. J. Organomet. Chem. 1985, 289, 425.
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Likhholov, V.A.4
Yermakov, Y.I.5
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21
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0025915188
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Oxidative Addition of H-N Bond in Amides: a) Hursthouse, M. B.; Mazid, M. A.; Robinson, S. D.; Sahajpal, A. J. Chem. Soc., Chem. Commun. 1991, 1146.
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Hursthouse, M.B.1
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Robinson, S.D.3
Sahajpal, A.4
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22
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37049081178
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DALTON TRANS
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b) Kurishima, S.; Matsuda, N.; Tamura, N.; Ito, T. J. chem. Soc. DALTON TRANS. 1991, 1135.
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Kurishima, S.1
Matsuda, N.2
Tamura, N.3
Ito, T.4
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23
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12044254150
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Glueck, D. S.; Wu, J. Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1991, 113, 2041.
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Glueck, D.S.1
Wu, J.2
Hollander, F.J.3
Bergman, R.G.4
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26
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0343301188
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One referee suggested that the role of acetic acid is to protonate the Pd-coordinated allene and facilitate nucleophilic attack by the amine
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One referee suggested that the role of acetic acid is to protonate the Pd-coordinated allene and facilitate nucleophilic attack by the amine.
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