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Transition-metal-catalyzed acetoxylation of heterocycles: all that glitters is not palladium

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Chemistry of Heterocyclic Compounds Aims and scope

Transition-metal-catalyzed regioselective oxidation of heteroaromatic C–H bonds is highlighted with emphasis on mechanistic issues.

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Notes

  1. Formation of 2,3-bisacetoxyindole side product was observed in AcOH (see [2]). Nevertheless, C-3 acetoxylated indole was the major product.

  2. Although there is a strong preference for the formation of pyrrolyliodonium salts at the C-2 position, the acetoxylation regioselectivity apparently was a result of the combined directing effects of pyrrole substituents.

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga, LV-1006, Latvia

    E. Suna

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  1. E. Suna
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 49-53, January, 2012.

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Suna, E. Transition-metal-catalyzed acetoxylation of heterocycles: all that glitters is not palladium. Chem Heterocycl Comp 48, 44–48 (2012). https://doi.org/10.1007/s10593-012-0967-5

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  • DOI: https://doi.org/10.1007/s10593-012-0967-5

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