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

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.

SUBMITTER: Kedrowski SM

PROVIDER: S-EPMC2941390 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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

Kedrowski Sean M A SM Dougherty Dennis A DA

Organic letters 20100901 18

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-f ...[more]

PMID: 20726566

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