4.4 Article

Simple and catalyst-free method for the synthesis of diaryl selenides by reactions of arylselenols and arenediazonium salts

Journal

TETRAHEDRON LETTERS
Volume 55, Issue 5, Pages 1057-1061

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.12.086

Keywords

Organoselenium compounds; Selenol; Arenediazonium salts; Hypophosphorous acid; Nucleophilic aromatic substitution

Funding

  1. FINEP
  2. CAPES
  3. CNPq [473165/2012-0]
  4. FAPERGS

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We describe here a simple and catalyst-free method to synthesize diaryl selenides by reaction of arenediazonium tetrafluoroborate salts with arylselenols, generated in situ by using diaryl diselenides and hypophosphorous acid (H3PO2), using THF as solvent. This is a direct nucleophilic aromatic substitution (SNAr) reaction performed with diary] diselenides and arenediazonium salts bearing electron-withdrawing and electron-donating groups affording the corresponding diaryl selenides in moderated to good yields. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.

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