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Addison-Wesley Longman Limited: Singapore
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(a) Gilchrist, T. L. Heterocyclic Chemistry; Addison-Wesley Longman Limited: Singapore, 1997.
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Heterocyclic Chemistry
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Gilchrist, T.L.1
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(a) Utimoto, K.; Miwa, H.; Nozaki, H. Tetrahedron Lett. 1981, 22, 4277-4278.
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Tetrahedron Lett.
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Utimoto, K.1
Miwa, H.2
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(b) Irtani, K.; Matsubara, S.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1799-1802.
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(c) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 2581-2584.
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Tetrahedron Lett.
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(d) Cacchi, S.; Carnicelli, V.; Marinelli, F. J. Organomet. Chem. 1994, 475, 289-296.
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Cacchi, S.1
Carnicelli, V.2
Marinelli, F.3
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0030908560
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Selected recent examples: (b) Chen, C.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676-2677. (c) Nazaré, M.; Schneider, C.; Lindenschmidt, A.; Will, D. W. Angew. Chem., Int. Ed. 2004, 43, 4526-4528. (d) Ackermann, L.; Kaspar, L. T.; Gschrei, C. J. Chem. Commun. 2004, 2824-2825.
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J. Org. Chem.
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Chen, C.1
Lieberman, D.R.2
Larsen, R.D.3
Verhoeven, T.R.4
Reider, P.J.5
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11
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4544224760
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Selected recent examples: (b) Chen, C.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676-2677. (c) Nazaré, M.; Schneider, C.; Lindenschmidt, A.; Will, D. W. Angew. Chem., Int. Ed. 2004, 43, 4526-4528. (d) Ackermann, L.; Kaspar, L. T.; Gschrei, C. J. Chem. Commun. 2004, 2824-2825.
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(2004)
Angew. Chem., Int. Ed.
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Nazaré, M.1
Schneider, C.2
Lindenschmidt, A.3
Will, D.W.4
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12
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11244303542
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Selected recent examples: (b) Chen, C.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676-2677. (c) Nazaré, M.; Schneider, C.; Lindenschmidt, A.; Will, D. W. Angew. Chem., Int. Ed. 2004, 43, 4526-4528. (d) Ackermann, L.; Kaspar, L. T.; Gschrei, C. J. Chem. Commun. 2004, 2824-2825.
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(2004)
Chem. Commun.
, pp. 2824-2825
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Ackermann, L.1
Kaspar, L.T.2
Gschrei, C.J.3
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13
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0042808535
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For a two-step, one-pot approach consisting of a hydroamination and a subsequent intramolecular palladium-catalyzed amination reaction, see: Siebenreicher, H.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 2003, 42, 3042-3044.
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Angew. Chem., Int. Ed.
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Siebenreicher, H.1
Bytschkov, I.2
Doye, S.3
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15
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0008842650
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Ricci, A., Ed.; Wiley-VCH: Weinheim
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(b) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000; pp 195-262.
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Modern Amination Methods
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Hartwig, J.F.1
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17
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(a) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488-2490.
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Angew. Chem., Int. Ed.
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Rodriguez, A.L.1
Koradin, C.2
Dohle, W.3
Knochel, P.4
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18
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0013168349
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(b) For a review, see: Seayad, J.; Tillack, A.; Hartung, C. G.; Beller, M. Adv. Synth. Catal. 2002, 344, 795-813.
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(2002)
Adv. Synth. Catal.
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Seayad, J.1
Tillack, A.2
Hartung, C.G.3
Beller, M.4
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19
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1242352490
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(a) For a recent example, see: Hiroya, K.; Itoh, S.; Sakamoto, T. J. Org. Chem. 2004, 69, 1126-1136.
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(2004)
J. Org. Chem.
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Hiroya, K.1
Itoh, S.2
Sakamoto, T.3
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20
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0038343546
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and references therein
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(b) See also: Barluenga, J.; Trincado, M.; González, J. Angew. Chem., Int. Ed. 2003, 42, 2406-2409 and references therein.
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(2003)
Angew. Chem., Int. Ed.
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Barluenga, J.1
Trincado, M.2
González, J.3
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21
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0001654457
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Early examples: (a) Castro, C. E.; Stephens, R. D. J. Org. Chem. 1963, 28, 2163. (b) Castro, C. E.; Gaughan, E. J.; Owsley, D. C. J. Org. Chem. 1966, 31, 4071-4078.
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J. Org. Chem.
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Castro, C.E.1
Stephens, R.D.2
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22
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0002082317
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Early examples: (a) Castro, C. E.; Stephens, R. D. J. Org. Chem. 1963, 28, 2163. (b) Castro, C. E.; Gaughan, E. J.; Owsley, D. C. J. Org. Chem. 1966, 31, 4071-4078.
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Castro, C.E.1
Gaughan, E.J.2
Owsley, D.C.3
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23
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0001152076
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For the use of heterocyclic carbene ligands in C-N bond-forming processes, see: (a) Huang, J.; Grasa, G.; Nolan, S. P. Org. Lett. 1999, 1, 1307-1309. (b) Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423-1426.
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(1999)
Org. Lett.
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Huang, J.1
Grasa, G.2
Nolan, S.P.3
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24
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0034682151
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For the use of heterocyclic carbene ligands in C-N bond-forming processes, see: (a) Huang, J.; Grasa, G.; Nolan, S. P. Org. Lett. 1999, 1, 1307-1309. (b) Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423-1426.
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Org. Lett.
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Stauffer, S.R.1
Lee, S.2
Stambuli, J.P.3
Hauck, S.I.4
Hartwig, J.F.5
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25
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5444275052
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de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim
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2 and CuI. For a review, see: Marsden, J. A.; Haley, M. M. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; pp 317-394.
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Metal-Catalyzed Cross-Coupling Reactions, 2nd Ed.
, pp. 317-394
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Marsden, J.A.1
Haley, M.M.2
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26
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13844249627
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note
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2O, 200/1) to yield 4a as a white solid (282 mg, 99%).
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27
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13844262026
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note
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4 led to complete conversion (4j: 40% isolated yield) and no conversion of the corresponding alkyne, respectively.
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29
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13844274327
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note
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4 instead of KO-t-Bu under otherwise identical conditions to the one outlined in Table 1, entry 8, yielded exclusively the corresponding amine 3, supporting the sequence outlined in Scheme 1.
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32
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0037201095
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Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Lett. 2002, 43, 7143-7146.
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(2002)
Tetrahedron Lett.
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Kelkar, A.A.1
Patil, N.M.2
Chaudhari, R.V.3
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33
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13844291786
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note
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2O, 200/1 → 50/1) to yield 4n as a yellow oil (195 mg, 67%).
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34
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0038276941
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For copper-catalyzed intramolecular amination reactions of aryl chlorides under mild conditions, see: Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793-796.
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(2003)
Org. Lett.
, vol.5
, pp. 793-796
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Kwong, F.Y.1
Buchwald, S.L.2
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35
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0035936728
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KO-t-Bu can assist similar cyclization reactions via formation of an aryne intermediate. See, for example: Beller, M.; Breindl, C.; Riermeier, T. H.; Tillack, A. J. Org. Chem. 2001, 66, 1403-1412.
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(2001)
J. Org. Chem.
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Beller, M.1
Breindl, C.2
Riermeier, T.H.3
Tillack, A.4
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36
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3242702454
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Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33, 302-312.
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(2004)
Chem. Soc. Rev.
, vol.33
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Lee, J.M.1
Na, Y.2
Han, H.3
Chang, S.4
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37
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0000187088
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For the use of N-heterocyclic carbene palladium complexes for Sonogashira coupling reactions, see: Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020-1022.
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(2002)
Organometallics
, vol.21
, pp. 1020-1022
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Yang, C.1
Nolan, S.P.2
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