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1
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0345708168
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For reviews, see
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For reviews, see: (a) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
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Angew. Chem., Int. Ed.
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Ley, S.V.1
Thomas, A.W.2
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2
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(b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
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Acc. Chem. Res.
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Wolfe, J.P.1
Wagaw, S.2
Marcoux, J.-F.3
Buchwald, S.L.4
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7
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For reviews, see
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For reviews, see: (a) Watson, I. D. G.; Yudin, A. K. Curr. Opin. Drug Discovery Dev. 2002, 5, 906.
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(2002)
Curr. Opin. Drug Discovery Dev.
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Watson, I.D.G.1
Yudin, A.K.2
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8
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(b) Dembeck, P.; Seconi, G.; Ricci, A. Chem. - Eur. J. 2000, 6, 1281.
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Chem. - Eur. J.
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Dembeck, P.1
Seconi, G.2
Ricci, A.3
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11
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0037958127
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(e) Greck, C.; Bischoff, L.; Ferreira, F.; Genêt, J. P. J. Org. Chem. 1995, 60, 7010.
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J. Org. Chem.
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, pp. 7010
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Greck, C.1
Bischoff, L.2
Ferreira, F.3
Genêt, J.P.4
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12
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0033593396
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(f) Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641.
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(1999)
J. Org. Chem.
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Bernardi, P.1
Dembech, P.2
Fabbri, G.3
Ricci, A.4
Seconi, G.5
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13
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4544325407
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(g) Sapountzis, I.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 897.
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Angew. Chem., Int. Ed.
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Sapountzis, I.1
Knochel, P.2
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14
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2442544350
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For Cu-catalyzed amination using hydroxylamines, see
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For Cu-catalyzed amination using hydroxylamines, see: (a) Berman, A. M.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 5680.
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(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 5680
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Berman, A.M.1
Johnson, J.S.2
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18
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22244441508
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For Ni-catalyzed amination using hydroxylamines, see
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For Ni-catalyzed amination using hydroxylamines, see: Berman, A. M.; Johnson, J. S. Synlett 2005, 1799.
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(2005)
Synlett
, pp. 1799
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Berman, A.M.1
Johnson, J.S.2
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19
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53349121032
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This method was not effective with 1a (11% yield)
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He, C.; Chen, C.; Cheng, J.; Liu, C.; Liu, W.; Li, Q.; Lei, A. Angew. Chem., Int. Ed. 2008, 47, 6414. This method was not effective with 1a (11% yield).
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(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 6414
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He, C.1
Chen, C.2
Cheng, J.3
Liu, C.4
Liu, W.5
Li, Q.6
Lei, A.7
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20
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37049033864
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N-Arylsuccinimide has been observed as a minor byproduct (8% yield) in NCS-mediated, Pd-catalyzed oxidative functionalization of C-H bonds. See
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N-Arylsuccinimide has been observed as a minor byproduct (8% yield) in NCS-mediated, Pd-catalyzed oxidative functionalization of C-H bonds. See: Whitfield, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 15142.
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(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 15142
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Whitfield, S.R.1
Sanford, M.S.2
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21
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12344259837
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N-Chloroamines can be prepared by treating the corresponding amines with bleach. See
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N-Chloroamines can be prepared by treating the corresponding amines with bleach. See: Zhong, Y.-L.; Zhou, H.; Gauthier, D. R.; Lee, J.; Askin, D.; Dolling, U. H.; Volante, R. P. Tetrahedron Lett. 2005, 46, 1099.
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(2005)
Tetrahedron Lett.
, vol.46
, pp. 1099
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Zhong, Y.-L.1
Zhou, H.2
Gauthier, D.R.3
Lee, J.4
Askin, D.5
Dolling, U.H.6
Volante, R.P.7
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22
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0001598172
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Our working hypothesis was based on a cross-coupling mechanism for the transformation that would be initiated by oxidative addition of the Ni catalyst into the N-Cl bond by a single-electron-transfer (SET) mechanism. For studies of oxidative addition of alkyl halides by an SET mechanism, see
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Our working hypothesis was based on a cross-coupling mechanism for the transformation that would be initiated by oxidative addition of the Ni catalyst into the N-Cl bond by a single-electron-transfer (SET) mechanism. For studies of oxidative addition of alkyl halides by an SET mechanism, see: (a) Stille, J. K.; Cowell, A. B. J. Organomet. Chem. 1977, 124, 253.
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(1977)
J. Organomet. Chem.
, vol.124
, pp. 253
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Stille, J.K.1
Cowell, A.B.2
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23
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33749519198
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(b) Jones, G. D.; Martin, J. L.; McFarland, C.; Allen, O. R.; Hall, R. E.; Haley, A. D.; Brancond, R. J.; Konovalova, T.; Desrochers, P. J.; Pulay, P.; Vicic, D. A. J. Am. Chem. Soc. 2006, 128, 13175.
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(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 13175
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Jones, G.D.1
Martin, J.L.2
McFarland, C.3
Allen, O.R.4
Hall, R.E.5
Haley, A.D.6
Brancond, R.J.7
Konovalova, T.8
Desrochers, P.J.9
Pulay, P.10
Vicic, D.A.11
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24
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0008927849
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For the reaction of NBS with Ni(0) complexes, see
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For the reaction of NBS with Ni(0) complexes, see: (c) Weston, C. W.; Verstuyft, A. W.; Nelson, J. H.; Jonassen, H. B. Inorg. Chem. 1977, 16, 1313.
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(1977)
Inorg. Chem.
, vol.16
, pp. 1313
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Weston, C.W.1
Verstuyft, A.W.2
Nelson, J.H.3
Jonassen, H.B.4
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25
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0001038041
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For reductive elimination of Ni amido complexes, see
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For reductive elimination of Ni amido complexes, see: (d) Koo, K.; Hillhouse, G. L. Organometallics 1995, 14, 4421.
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(1995)
Organometallics
, vol.14
, pp. 4421
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Koo, K.1
Hillhouse, G.L.2
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26
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70350640000
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note
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N2 attack of an arylnickel complex on the N-chloroamine (see ref 3d).
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27
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70350661234
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note
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DMA appears to play a key role in the reaction.
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28
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70350623662
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note
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See the Supporting Information for details of the ligand screen.
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29
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0008854673
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N-Chloroamines are known to oxidize phosphines. See
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N-Chloroamines are known to oxidize phosphines. See: Sopchik, A. E.; Bentrude, W. G. Tetrahedron Lett. 1980, 21, 4679.
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(1980)
Tetrahedron Lett.
, vol.21
, pp. 4679
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Sopchik, A.E.1
Bentrude, W.G.2
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30
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70350677386
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note
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In the absence of Ni(cod)2 and/or bipyridine, reaction of 1a with diphenylzinc under the standard reaction conditions afforded <5% yield of 3a.
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31
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70350667046
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note
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1H NMR spectroscopy of the unpurified reaction mixture revealed that benzaldehyde was formed in 23% yield in this reaction. Its formation is tentatively attributed to β-hydride elimination from a Ni amido complex to form N-methylbenzaldimine, which was hydrolyzed upon aqueous workup.
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32
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0347694968
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Electron-withdrawing substituents on N substantially slow the reductive elimination from arylpalladium amido complexes. See
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Electron-withdrawing substituents on N substantially slow the reductive elimination from arylpalladium amido complexes. See: Yamashita, M.; Cuevas Vicario, J. V.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 16347.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 16347
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Yamashita, M.1
Cuevas Vicario, J.V.2
Hartwig, J.F.3
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36
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70350625782
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note
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Cyclization of these substrates frequently proceeds by a radical mechanism (see ref 16c).
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37
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70350681507
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note
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Preparation of 1j takes advantage of the chemoselectivity of the N-chlorination reaction toward the more nucleophilic nitrogen.
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