4.4 Article

A procedure for Appel halogenations and dehydrations using a polystyrene supported phosphine oxide

Journal

TETRAHEDRON LETTERS
Volume 55, Issue 4, Pages 799-802

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.11.098

Keywords

Phosphine oxides; Halogenation; Polymeric reagents; Chlorophosphonium salts

Funding

  1. University of Nottingham
  2. EPSRC [EP/J000868/1]
  3. EPSRC [EP/H018034/1, EP/J000868/1, EP/K031082/1] Funding Source: UKRI
  4. Engineering and Physical Sciences Research Council [EP/J000868/1, EP/H018034/1, EP/K031082/1] Funding Source: researchfish

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The conversion of a commercially available polystyrene supported phosphine oxide into synthetically useful polymeric halophosphonium salts using oxalyl chloride/bromide takes place at room temperature in 5 min and generates only CO and CO2 as by-products. The polymeric halophosphonium salts so obtained are useful reagents for Appel halogenations and other dehydrative coupling reactions. This gives rise to a simple three-step synthesis cycle for Appel and related reactions using a commercially available polymeric phosphine oxide with very simple purification and no phosphorus waste. (C) 2013 Elsevier Ltd. All rights reserved.

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