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To the best of our knowledge, 1,4-additions of indoles to enones occurring via SET have not been reported in the literature. For related, specific photoinduced additions of indoles, see the following. To 1-methyl-2-pyridone: (a) Ohmiya, S.; Noguchi, M.; Ina, S.; Kubo, H.; Otomasu, H. Chem. Pharm. Bull. 1992, 40, 854.
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To 3-acetyl-6-nitrocoumarin (solid state): (c) Du, D.-M.; Wang, Y.-M.; Meng, J.-B.; Zhou, X.-Z.; Zhang, H., P. Gaodeng Xuexiao Huaxue Xuebao 1996, 17, 252 (CAS 124:189184).
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(d) Wang, Y.-M.; Du, D.-M.; Li, X.-L.; Meng, J.-B.; Zhou, X.-Z. Yonji Huaxue 1997, 17, 433 (CAS 128:28491).
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The scope of these reactions has also been extended through the use of sensitizers such as 9,10-dicyanthracene. For more examples and a detailed discussion, see: Jeon, Y. T.; Lee, C.-P.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 8847.
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note
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See Experimental Section for details.
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note
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A more detailed mechanistic discussion can be found in the Supporting Information.
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36
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note
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The described transformations were typically accompanied by a change in color front a clear to a red or an amber solution.
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