Abstract
AbstractEmploying a photoremovable protecting group is a useful technique to achieve precise conditional control over a biological function. This Communication reports the development of a photoremovable protecting group for the nitrile moiety. In the process, O‐(arylcarbonyl) oxime was photochemically converted into the corresponding nitrile in the presence of a carbazole photosensitizer by means of an electron transfer from the excited carbazole to the arylcarbonyl unit. A variety of alkyl and (hetero) aryl nitriles were generated from the corresponding O‐(arylcarbonyl) oximes. Moreover, a self‐contained variant, in which O‐(arylcarbonyl) oxime and carbazole units were covalently bonded, exhibited photochemical nitrile formation even in a highly diluted aqueous solution (0.1 mM), thus demonstrating that this molecular motif is potentially applicable in biological systems.
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