M. S. Smyth, H. Ford, T. Burke
Jul 14, 1992
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Journal
Tetrahedron Letters
Abstract
Abstract Methodology is presented for the preparation of heretofore unreported benzylic α,α-difluorophosphonic acids. Oxidation of benzylic α-hydroxyphosphonates using MnO 2 , provided a new route for the synthesis of benzylic α-oxophosphonates, which were then fluorinated using DAST. Hydrolysis of ester protecting groups yielded α,α-difluorophosphonic acids. These represent non-hydrolyzable mimetics of arylphosphates which could be of value in the study of cellular phosphotyrosine-utilizing signal transduction pathways.