Light-Controlled Orthogonal Covalent Bond Formation at Two Different Wavelengths

Abstract

We report light-induced reactions in a two-chromophore system capable of sequence-independent λ-orthogonal reactivity relying solely on the choice of wavelength and solvent. In a solution of water and acetonitrile, LED irradiation at λmax=285 nm leads to full conversion of 2,5-diphenyltetrazoles with N-ethylmaleimide to the pyrazoline ligation products. Simultaneously present o-methylbenzaldehyde thioethers are retained. Conversely, LED irradiation at λmax=382 nm is used to induce ligation of the o-methylbenzaldehydes in acetonitrile with N-ethylmaleimide via o-quinodimethanes, while 2,5-diphenyltetrazoles also present are retained. This unprecedented photochemical selectivity is achieved through control of the number and wavelength of incident photons as well as favorable optical properties and quantum yields of the reactants in their environment.