Nucleoside Arylation Using Base-Free Cross-Coupling Reactions
The discovery of new organophosphorus compounds is of current interest to the synthetic community. Of the current methods available for the synthesis of arylphosphonates, only a few low temperature approaches are known. Since many biomolecules are not stable at the elevated temperatures typically required for the preparation of arylphosphonates, the development of a high yielding method that is tolerant to a wide range of functional groups and functions at low temperatures would offer scientists a valuable way to prepare new derivatives with altered bioactivity. In the course of our investigation, we have also discovered a rare low temperature P-H activation reaction involving secondary phosphites and organometallic compounds. This presentation will focus on the generation of P-metallated nucleosides and their use in base-free cross-coupling reactions that result in the formation of unique arylated nucleosides.