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Examples of powerful C-H activations utilizing acetanilides as substrates
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79251589970
-
-
In contrast, benzaldehydes do not react under these conditions
-
In contrast, benzaldehydes do not react under these conditions.
-
-
-
-
70
-
-
79251565273
-
-
Small amounts of di-olefination products are generally observed, together with significant amounts of unreacted starting material
-
Small amounts of di-olefination products are generally observed, together with significant amounts of unreacted starting material.
-
-
-
-
71
-
-
79251576843
-
-
See the Supporting Information
-
See the Supporting Information.
-
-
-
-
72
-
-
79251574694
-
-
note
-
[10a,a13]
-
-
-
-
73
-
-
79251566798
-
-
note
-
For a recent example of the selective activation of indoles at the 2-H position through the palladium-catalyzed oxidative Heck reaction, see
-
-
-
-
74
-
-
77955837658
-
-
for the general reactivity of indoles, see
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García-Rubia, A.1
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0004061172
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4th ed., Blackwell, Oxford, chap. and 17.
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Heterocyclic Chemistry
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-
Joule, J.A.1
Mills, K.2
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76
-
-
79251592587
-
-
note
-
Importantly, under our standard reaction conditions, N-methylindole did not react with styrene, indicating the compatibility of the 2-H and 3-H positions of the indole with this method.
-
-
-
-
77
-
-
79251569002
-
-
The strategic use of the rhodium-catalyzed functionalization of acetanilides can be further illustrated by Equation (6)
-
The strategic use of the rhodium-catalyzed functionalization of acetanilides can be further illustrated by Equation (6).
-
-
-
-
78
-
-
79251565870
-
-
note
-
[10a] Indole products 1ab and 1ac, however, have been prepared by us with only 0.5 mola% of the rhodium catalyst precursor.
-
-
-
-
79
-
-
79251582558
-
-
note
-
2], dioxane, 140a°C, 16 h).
-
-
-
-
80
-
-
77952578429
-
-
For a related exo cyclization in a palladium-catalyzed oxidative Heck reaction using hydroxy directing groups, see.
-
For a related exo cyclization in a palladium-catalyzed oxidative Heck reaction using hydroxy directing groups, see:, Y. Lu, D.-H. Wang, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 5916.
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81
-
-
79251581915
-
-
note
-
Utilization of the secondary amide N-Me- 3am under standard conditions resulted in the formation of the corresponding product N-Me- 4ac in 38a% yield with a reversed E/Z ratio of 7:1.
-
-
-
|