Photorelease of phosphates: Mild methods for protecting phosphate derivatives

• Sanjeewa N. Senadheera,
• Abraham L. Yousef and
• Richard S. Givens

Beilstein J. Org. Chem. 2014, 10, 2038–2054, doi:10.3762/bjoc.10.212

• to completion. The 2,6-naphthyl ketone platform instead remains intact whereas the quinolin-5-yl ketone fragments to a much more complex, highly absorbing reaction mixture that competes for the incident light. Keywords: caged phosphates; hydroxynaphthylacetyl; organophosphorus; photo-Favorskii

• chromophores, benzoin, pHP, and now 1,4-hydroxynaphthylacetyl substrates cleanly undergo rearrangements that shift the absorption chromophore. Benzoins form benzofurans that, in fact, exacerbate the problem of light competition and fluorescence. Only pHP and 1,4-substituted naphthylacetyl 14 generate a less