Palladium-Catalyzed Dehydrative Allylation of Hypophosphorous Acid with Allylic Alcohols

Karla Bravo-Altamirano and Jean-Luc Montchamp*
Department of Chemistry, Box 298860, Texas Christian University, Fort Worth, Texas 76129
Org. Lett., 2006, 8 (18), pp 4169–4171
DOI: 10.1021/ol061828e
Publication Date (Web): August 10, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, j.montchamp@tcu.edu

Abstract

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A novel palladium-catalyzed allylation of H3PO2 with allylic alcohols is described. The phosphorus−carbon bond-forming reaction produces allylic-H-phosphinic acids and water, in the absence of additives. Primary H-phosphinic acids are obtained in excellent yields, whereas secondary H-phosphinic acids react sluggishly. A reusable polymer-supported catalyst is also described. The reaction provides an environmentally sound approach to H-phosphinic acids.

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History

  • Published In Issue August 31, 2006
  • Received July 24, 2006

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