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See Supporting Information for full experimental details.
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See Supporting Information for full experimental details.
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37
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33646501936
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The Arndtsen group has attributed amide formation to thermal decomposition of the iminium ion. See
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2 and no Ni(0) catalyst, the cyclization of N -(p -methoxybenzoyl)aminal 1i resulted in only 3% yield of isoindolinone 3i.
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2 and no Ni(0) catalyst, the cyclization of N -(p -methoxybenzoyl)aminal 1i resulted in only 3% yield of isoindolinone 3i.
-
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39
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79959739200
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2 resulted in complete decomposition of aminal 1a. Significant decomposition of aminal 1a to amide 4 was observed under these conditions, but no isoindolinone 3a was observed.
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2 resulted in complete decomposition of aminal 1a. Significant decomposition of aminal 1a to amide 4 was observed under these conditions, but no isoindolinone 3a was observed.
-
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40
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79959722937
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This result is consistent with observations of Doyle's Ni-catalyzed cross-coupling of related aminal substrates. See ref 13.
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This result is consistent with observations of Doyle's Ni-catalyzed cross-coupling of related aminal substrates. See ref 13.
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Similar mechanistic quandries have been proposed for related Pd-catalyzed cyclizations. See
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