-
5
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0000826734
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-
For examples of pyrrolidine synthesis that involve intramolecular C-N bond formation and intermolecular C-C bond formation, see: (a) Y. Tamaru, and M. Kimura Synlett 1997 749 757
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(1997)
Synlett
, pp. 749-757
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Tamaru, Y.1
Kimura, M.2
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10
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7444269099
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For related transformations that afford indoline or tetrahydrofuran products, see: (a) R. Lira, and J.P. Wolfe J. Am. Chem. Soc. 126 2004 13906 13907
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(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 13906-13907
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Lira, R.1
Wolfe, J.P.2
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12
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0001080997
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Several examples of cleavage of p-methoxyphenyl groups from nitrogen have been described. However, these transformations are typically facilitated by the use of strong oxidants and exhibit relatively low functional group tolerance. See: (a) S. Saito, K. Hatanaka, and H. Yamamoto Org. Lett. 2 2000 1891 1894
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(2000)
Org. Lett.
, vol.2
, pp. 1891-1894
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-
Saito, S.1
Hatanaka, K.2
Yamamoto, H.3
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16
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20444467459
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-
note
-
Dpe-phos=bis(2-diphenylphosphinophenyl) ether. Dppf=1,1′- bis(diphenylphosphinoferrocene). Xantphos=9,9-dimethyl-4,5- bis(diphenylphosphino) xanthene. Dppe=1,2-bis(diphenylphosphino) ethane. Dppb=1,4-bis(diphenylphosphino) butane. Nixantphos=4,6-bis(diphenylphosphino) phenoxazine.
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19
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0042291889
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D. Astruc Wiley-VCH Weinhem, Germany
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J.F. Hartwig D. Astruc Modern Arene Chemistry 2002 Wiley-VCH Weinhem, Germany 107 168
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(2002)
Modern Arene Chemistry
, pp. 107-168
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Hartwig, J.F.1
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20
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0025029284
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Balme has previously described the Pd/dppp-catalyzed Heck arylation of 4a with iodobenzene. See: G. Fournet, G. Balme, and J. Gore Tetrahedron 46 1990 7763 7774
-
(1990)
Tetrahedron
, vol.46
, pp. 7763-7774
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Fournet, G.1
Balme, G.2
Gore, J.3
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22
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20444495080
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note
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Control experiments demonstrated the Boc-cleavage is base-induced (not Pd-catalyzed). See Ref. 12.
-
-
-
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23
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20444490138
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note
-
The product isolated from this reaction contained ca 15% of the corresponding dihydropyrrole. Similar side reactions have been previously observed in reactions of 2-allylaniline or γ-N-arylaminoalkenes with electron-rich aryl bromides. See Refs. 4,5a.
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-
-
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25
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0842305925
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For recent studies on Pd-catalyzed N-vinylation of amines, See: J. Barluenga, M.A. Fernández, F. Aznar, and C. Valdes Chem. Eur. J. 10 2004 494 507
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(2004)
Chem. Eur. J.
, vol.10
, pp. 494-507
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-
Barluenga, J.1
Fernández, M.A.2
Aznar, F.3
Valdes, C.4
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26
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20444473940
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note
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The base induced substrate olefin isomerization was only observed in reactions of 2-allylaniline derivatives.
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27
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33947093389
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For Pd-catalyzed oxidative amination reactions that afford indole products, see: (a) L.S. Hegedus, G.F. Allen, J.J. Bozell, and E.L. Waterman J. Am. Chem. Soc. 100 1978 5800 5807
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(1978)
J. Am. Chem. Soc.
, vol.100
, pp. 5800-5807
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Hegedus, L.S.1
Allen, G.F.2
Bozell, J.J.3
Waterman, E.L.4
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29
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20444443337
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-
note
-
Proton NMR analysis of crude reaction mixtures revealed diastereomer ratios of 10-20:1; the minor diastereomer was usually readily separated by chromatography to provide isolated products with >20:1 dr. Thus, diastereomeric ratios reported in Table 4 represent ratios of diastereomers for the isolated material upon which the yield is based. The diastereomeric ratios observed in crude reaction mixtures were >20:1 for 2,5-disubstituted pyrrolidines, >20:1 for 6-substituted hexahydrocyclopenta[b]pyrroles, and ca 10:1 for 2,3-disubstituted pyrrolidines.
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30
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20444477708
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note
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1H NMR analysis.
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-
-
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31
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20444433347
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note
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The Pd/dpe-phos-catalyzed reaction of a N-Boc protected substrate bearing an internal acyclic alkene afforded a single pyrrolidine product, albeit in low yield (ca 20%).
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37
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20444442934
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note
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Although we currently favor this mechanistic hypothesis, an alternate mechanism involving alkene insertion into the Pd-C bond of 33 followed by C-N bond-forming reductive elimination cannot be excluded in all transformations.
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40
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0035901629
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M. Oestreich, P.R. Dennison, J.J. Kodanko, and L.E. Overman Angew. Chem., Int. Ed. 40 2001 1439 1442
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Angew. Chem., Int. Ed.
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, pp. 1439-1442
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Oestreich, M.1
Dennison, P.R.2
Kodanko, J.J.3
Overman, L.E.4
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41
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0037239486
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B. Clique, C.H. Fabritius, C. Couturier, N. Monteiro, and G. Balme Chem. Commun. 2003 272 273
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Chem. Commun.
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Clique, B.1
Fabritius, C.H.2
Couturier, C.3
Monteiro, N.4
Balme, G.5
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42
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0038276962
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Electron-donating groups may facilitate β-hydride elimination by stabilizing the developing positive charge on the β-carbon in the transition state. See: J.A. Mueller, and M.S. Sigman J. Am. Chem. Soc. 125 2003 7005 7013
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J. Am. Chem. Soc.
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, pp. 7005-7013
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Mueller, J.A.1
Sigman, M.S.2
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43
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20444457375
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note
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The small size of the N-acyl and N-Boc substituents relative to N-aryl groups may also alter the rate of β-hydride elimination in some systems.
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53
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0141786829
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G.D. Tebben, K. Rauch, C. Stratmann, C.M. Williams, and A. de Meijere Org. Lett. 5 2003 483 486
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Tebben, G.D.1
Rauch, K.2
Stratmann, C.3
Williams, C.M.4
De Meijere, A.5
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A. Eddaif, A. Laurent, P. Mison, N. Pellissier, P.A. Carrupt, and P. Vogel J. Org. Chem. 52 1987 5548 5560
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