Synthesis of (purin-6-yl)methylphosphonate bases and nucleosides

Surface Modification Using Phosphonic Acids and Esters

“…On the other hand, the Michaelis–Becker reaction has also become the reaction of choice for the synthesis of dialkyl esters of alkylphosphonic acids, using in this case secondary phosphite reagents (Scheme ) . This synthetic protocol can be for example attractive in the case of heat-sensitive substrates, since this reaction can most often be performed at room temperature. − …”

Review on Modern Advances of Chemical Methods for the Introduction of a Phosphonic Acid Group

“…The Michaelis–Becker reaction is similar to the Arbuzov reaction in the sense that an alkyl halide or equivalent is the electrophile; however, instead of using a trialkyl phosphite as the nucleophile a dialkyl phosphonate is used in presence of a base (Table ). , The most often applied base is NaH, which deprotonates the phosphate, thereby enabling nucleophilic attack on the electrophilic alkyl halide via an S N 2 pathway.…”

A modular approach for the installation of functionalized phosphonates to heterocycles

“…Benzyl protected 6chloropurine underwent the SNAr with triethyl acetophosphonate smoothly to access 41 in moderate yield. A methylene variant of 41 (without CO2Et) has been previously prepared in 4 steps from commercially available reagents, 42 a stark contrast to the use of phosphonate -anion SNAr. The methylene variant can theoretically be made accessible using an SNAr-decarboxylation sequence (2 steps).…”