Journal of Organic Chemistry 2011-04-15

Direct conversion of benzylic and allylic alcohols to phosphonates.

Rocky J Barney, Rebekah M Richardson, David F Wiemer

Index: J. Org. Chem. 76(8) , 2875-9, (2011)

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Abstract

Benzyl phosphonate esters often serve as reagents in Horner-Wadsworth-Emmons reactions. In most cases, they can be prepared from benzylic alcohols via formation of the corresponding halide followed by an Arbuzov reaction. To identify a more direct synthesis of phosphonate esters, we have developed a one-flask procedure for conversion of benzylic and allylic alcohols to the corresponding phosphonates through treatment with triethyl phosphite and ZnI(2).