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. 2010 Sep 17;12(18):3990-3.
doi: 10.1021/ol1015493.

Room-temperature alternative to the Arbuzov reaction: the reductive deoxygenation of acyl phosphonates

Sean M A Kedrowski  1 , Dennis A Dougherty
Affiliations

Room-temperature alternative to the Arbuzov reaction: the reductive deoxygenation of acyl phosphonates

Sean M A Kedrowski et al. Org Lett. .

Abstract

The reductive deoxygenation of acyl phosphonates using a Wolff-Kishner-like sequence is described. This transformation allows direct access to alkyl phosphonates from acyl phosphonates at room temperature. The method can be combined with acyl phosphonate synthesis into a one pot, four-step procedure for the conversion of carboxylic acids into alkyl phosphonates. The methodology works well for a variety of aliphatic acids and shows a functional group tolerance similar to that of other hydrazone-forming reactions.

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Figures

Scheme 1
Scheme 1
The Arbuzov Reaction
Scheme 2
Scheme 2
Retrosynthesis of Alkyl Phosphonates from Carboxylic Acids
Scheme 3
Scheme 3
The Electron-Withdrawing Phosphonate Stabilizes the Carbanionic Character of the Key Intermediate
Scheme 4
Scheme 4
The Reaction Course of Acyl Phosphonates with Hydrazine is pH-Dependent
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    1. Also known as the Michaelis-Arbuzov reaction.

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