The scope of this method was exemplified by the preparation of 19 different phosphorylated alcohols (Table ). It is worth noting that, most of the older papers in this field present only analysis based on melting point and elemental analysis (occasionally 31 P NMR). More recent disclosures, with very few notable exceptions, 8c,9c,10a,11 usually do not include high resolution images of NMR spectra. It is also common that such methodology papers report only conversions not isolated yields, presumably due to the difficulty in handling those polar substances. To be sure, multiple methods have been reported for the purification of phosphates including: HPLC, 11a HILIC, 10a solid phase ion exchange, 9c,10a and recrystallization. We found that in small scale experiments HPLC was superior (see SI for column and eluent conditions) whereas HILIC was the method of choice for larger scale preparations or for compounds that are extremely polar. In some cases, it was convenient to isolate phosphates as their ammonium salts. As indicated in Table , simple amines are tolerated in this reaction (5, 14, 15) as well as basic heterocycles (16, 19). Alkynes (7), azides (8), thiophenes (9), aryl iodides (10), olefins (11), alkyl halides (12, 13), nitro arenes (17, 19), and indoline (18) were unscathed upon P-O bond formation. Finally, four medicinally relevant substrates were phosphorylated (Table ): metronidazole (19), AZT (20), cholesterol (21), and a tyrosine-containing peptide bearing histidine, aspartamide, and glutamide side-chains. Prior routes to some of these compounds were either laborious or contained limited experimental data such as the preparation of 7 (three steps, utility in biomolecule functionalization), 14 (three steps), <35% yield 24a or multistep procedures 24b,c with one paper showing higher yield with POCl3 and characterization based only on UV spectrum; 24d enhanced HIV1 activity reported ), and 21 (one 10c and three step routes given with little characterization data). The limitations of this reaction (see SI for details) stem from lack of tolerance of preexisting functionality on the alcohol to basic conditions, and lower nucleophilicity of sterically hindered substrates (i.e. tertiary alcohols).