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Fe(III)-Catalyzed direct C3 chalcogenylation of indole: The effect of iodide ions
Authors:Eduardo Q. Luz  Diego Seckler  Janylson Souza Araújo  Leonardo Angst  David B. Lima  Elise Ane Maluf Rios  Ronny R. Ribeiro  Daniel S. Rampon
Affiliation:1. Laboratory of Polymers and Molecular Catalysis (LAPOCA), Department of Chemistry, Federal University of Paraná–UFPR, P. O. Box 19032, Curitiba, PR, 81531-990, Brazil;2. Department of Chemistry, Federal University of Paraná–UFPR, P. O. Box 19032, Curitiba, PR, 81531-990, Brazil
Abstract:A mild and efficient iron (III)-catalyzed C3 chalcogenylation of indoles has been developed and the role of the iodide ions in this transformation was investigated. EPR experiments revealed the reduction of Fe(III) to Fe(II) under the reaction conditions, supporting the formation of molecular iodine in the system, which in effect catalyze the reaction. The scope of the chalcogenylation was broad and the synthesis of more functionalized 3-selenylindoles was explored.
Keywords:Direct chalcogenylation  Indoles  3-Selenylindoles  Iron (III)  Iodides
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