Journal of the American Chemical Society, Vol.139, No.13, 4655-4658, 2017
A General Strategy for Visible-Light Decaging Based on the Quinone Trimethyl Lock
Visible-light triggered quinone trimethyl locks are reported as a general design for long-wavelength photoremovable protecting groups for alcohols and amines. Intramolecular photoreduction unmasks a reactive phenol that undergoes fast lactonization to release alcohols and amines. Model substrates are released in quantitative yield along with well-defined, colorless hydroquinone byproducts. Substituent modifications of the quinone core allow absorption from 400 to 600 nm.