A General Strategy for Visible-Light Decaging Based on the Quinone Trimethyl Lock,Journal of the American Chemical Society

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A General Strategy for Visible-Light Decaging Based on the Quinone Trimethyl Lock
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2017-03-24 , DOI: 10.1021/jacs.7b01548
David P. Walton ₁ , Dennis A. Dougherty ₁

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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.

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