Chemoselective triazole-phosphonamidate conjugates suitable for photorelease.

Herein, we describe a new method for the conjugation of azide-containing target compounds that can be readily released as amines by irradiation with near UV light. This concept is based on a two-step protocol employing the chemoselective CuAAC and Staudinger-phosphonite reactions to deliver photo-cleavable phosphonamidate conjugates in high yields starting from 2-nitrobenzyl substituted phosphonites.

Controlled thioamide vs. amide formation in the thioacid-azide reaction under acidic aqueous conditions.

The thioacid-azide reaction and its chemoselectivity were probed with alkyl azides for a potential application to form amide bonds in aqueous solvents. Our results reveal that under acidic conditions thioamides were formed as major reaction products suggesting a competing mechanism, whereas reactions forming amides predominated at slightly higher pH values.