Stoichiometric Nitroxyl Photorelease Using the (6-Hydroxy-2-naphthalenyl)methyl Phototrigger

The design and synthesis of a photoactivatable HNO donor incorporating the (6-hydroxynaphthalen-2-yl)­methyl (6,2-HNM) photocage coupled to the trifluoromethanesulfonamidoxy analogue of the well-established HNO generator Piloty’s acid is described. The photoactive HNO donor stoichiometrically generates HNO (∼98%) at neutral pH conditions, and evidence for concerted C–O and N–S bond cleavage was obtained. The methanesulfonamidoxy analogue primarily undergoes undesired N–O bond cleavage.