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Issue 10, 2011
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Synthesis of diaryl selenides using electrophilic selenium species and nucleophilic boron reagents in ionic liquids

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Abstract

We described herein the use of imidazolium ionic liquids [bmim]PF6 and [bmim]BF4 in the selective, metal and catalyst-free synthesis of unsymmetrical diaryl selenides by electrophilic substitution in arylboron reagents with arylselenium halides (Cl and Br) at room temperature. This is a general substitution reaction and it was performed with arylboronic acids or potassium aryltrifluoroborates bearing electron-withdrawing or electron-donating groups, affording the corresponding diaryl selenides in good to excellent yields. The ionic liquid [bmim][PF6] was easily recovered and utilized for further substitution reactions.

Graphical abstract: Synthesis of diaryl selenides using electrophilic selenium species and nucleophilic boron reagents in ionic liquids

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Publication details

The article was received on 20 Jun 2011, accepted on 19 Jul 2011 and first published on 22 Aug 2011


Article type: Paper
DOI: 10.1039/C1GC15725F
Citation: Green Chem., 2011,13, 2931-2938
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    Synthesis of diaryl selenides using electrophilic selenium species and nucleophilic boron reagents in ionic liquids

    C. S. Freitas, A. M. Barcellos, V. G. Ricordi, J. M. Pena, G. Perin, R. G. Jacob, E. J. Lenardão and D. Alves, Green Chem., 2011, 13, 2931
    DOI: 10.1039/C1GC15725F

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