New and Efficient Synthesis of 1,3-Dienylphosphonates by Palladium-Catalyzed Substitution of Propargylic Esters to Diethyl Phosphite

Abstract

An efficient route to the synthesis of 1,3-dienylphosphonates (1) has been developed for the first time by the substitution of propargylic esters (2) to the diethyl phosphite (3) nucleophile in the presence of Pd₂(dba)₃ · CHCl₃ (2 mol %) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (4 mol%). Both the alkyl and aryl 1,3-dienylphosphonates can be prepared from this transformation.

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GRAPHICAL ABSTRACT

Keywords:

• 1,3-Dienylphosphonates
• diethyl phosphite
• Pd-catalyzed
• propargylic substitution

ACKNOWLEDGMENTS

The authors are grateful for the financial support from the Scientific Research Project of the Department of Education of Liaoning Province of China (L2010048) and the Planned Science and Technology Project of Dalian (2011J21DW010).