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For reviews on Pd-catalyzed carboamination reactions, see
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For reviews on Pd-catalyzed carboamination reactions, see: Wolfe, J. P. Eur. J. Org. Chem. 2007, 571
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For related syntheses of imidazolidin-2-ones, isoxazolidines, pyrazolidines, piperazines, and morpholines via Pd-catalyzed carboamination reactions, see
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For related syntheses of imidazolidin-2-ones, isoxazolidines, pyrazolidines, piperazines, and morpholines via Pd-catalyzed carboamination reactions, see: Fritz, J. A.; Wolfe, J. P. Tetrahedron 2008, 64, 6838
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38349162901
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For Cu- or Au-catalyzed carboamination reactions, see
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For Cu- or Au-catalyzed carboamination reactions, see: Fuller, P. H.; Chemler, S. R. Org. Lett. 2007, 9, 5477
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Fuller, P.H.1
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Zhang, G.1
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19
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67650507268
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For alkene carboamination reactions involving solvent C?H bond functionalization, see
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For alkene carboamination reactions involving solvent C?H bond functionalization, see: Rosewall, C. F.; Sibbald, P. A.; Liskin, D. V.; Michael, F. E. J. Am. Chem. Soc. 2009, 131, 9488
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Sibbald, P. A.; Rosewall, C. F.; Swartz, R. D.; Michael, F. E. J. Am. Chem. Soc. 2009, 131, 15945
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21
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70349934214
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The use of aryl chlorides as electrophiles in Pd-catalyzed carboamination reactions that afford aziridines or pyrrolizidin-2-ones has recently been reported. See
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The use of aryl chlorides as electrophiles in Pd-catalyzed carboamination reactions that afford aziridines or pyrrolizidin-2-ones has recently been reported. See: Hayashi, S.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2009, 48, 7224
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Bagnoli, L.; Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Scarponi, C.; Tiecco, M. J. Org. Chem. 2010, 75, 2134
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Bedford, R. B.; Cazin, C. S. J.; Holder, D. Coord. Chem. Rev. 2004, 248, 2283
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0037112673
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52049105452
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0037122141
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0345802559
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42149091775
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references cited therein
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Reddy, C. V.; Kingston, J. V.; Verkade, J. G. J. Org. Chem. 2008, 73, 3047 and references cited therein.
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30
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77950964836
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Note
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1H NMR suggests that mixtures of pyrrolidine regioisomers are formed, and competing substrate N -arylation also occurs. This outcome may be due to a combination of relatively slow aminopalladation of the more hindered internal alkene combined with relatively slow reductive elimination from a secondary alkylpalladium intermediate analogous to II.
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31
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77950976731
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The installation of the aryl group at C5 rather than C6 in 2f ? g results from β-hydride elimination/hydridopalladation processes similar to those illustrated in Scheme 1 (II → IV → 3 ? 5). Selective formation of the 6-aryl isomers has been ascribed to the relative stabilities of intermediates along this pathway. For a detailed discussion of reaction mechanism and the origin of these products, see ref 1c
-
The installation of the aryl group at C5 rather than C6 in 2f ? g results from β-hydride elimination/hydridopalladation processes similar to those illustrated in Scheme 1 (II → IV → 3 ? 5). Selective formation of the 6-aryl isomers has been ascribed to the relative stabilities of intermediates along this pathway. For a detailed discussion of reaction mechanism and the origin of these products, see ref 1c.
-
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34
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77950965451
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The reactivity of intermediates I and II is highly dependent on ligand structure. For further discussion, see refs 1c and 2a
-
The reactivity of intermediates I and II is highly dependent on ligand structure. For further discussion, see refs 1c and 2a.
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35
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77950974847
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S-Phos = 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′- biphenyl
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S-Phos = 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′- biphenyl.
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36
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3042654141
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Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871
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Walker, S.D.1
Barder, T.E.2
Martinelli, J.R.3
Buchwald, S.L.4
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38
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0347653089
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1H NMR showed predominantly the desired product, with little or no evidence of side product formation. Modest yields obtained in some transformations may be due to base-mediated substrate decomposition. See
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1H NMR showed predominantly the desired product, with little or no evidence of side product formation. Modest yields obtained in some transformations may be due to base-mediated substrate decomposition. See: Tom, N. J.; Simon, W. M.; Frost, H. N.; Ewing, M. Tetrahedron Lett. 2004, 45, 905
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(2004)
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Tom, N.J.1
Simon, W.M.2
Frost, H.N.3
Ewing, M.4
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39
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17444400818
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Note
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3 as ligand, see ref 3e. For transformations that generate trans -2,5-disubstituted tetrahydrofurans using bis(2-diphenylphosphinophenyl)ether (dpe-phos) as ligand, see: Hay, M. B.; Hardin, A. R.; Wolfe, J. P. J. Org. Chem. 2005, 70, 3099
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Hay, M.B.1
Hardin, A.R.2
Wolfe, J.P.3
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40
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77950968137
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Efforts to employ a Boc-protected analogue of 13 also failed to provide a substituted morpholine product. Base-mediated decomposition of the substrate was observed
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Efforts to employ a Boc-protected analogue of 13 also failed to provide a substituted morpholine product. Base-mediated decomposition of the substrate was observed.
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