1. Unveiling Latent Photoreactivity of Imines
- Author
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Takafumi Enomoto, Yuto Tsuchiya, Daisuke Yokogawa, Tsuyoshi Ohtani, Takashi Ooi, Daisuke Uraguchi, and Shigeyuki Masaoka
- Subjects
010405 organic chemistry ,Chemistry ,General Medicine ,General Chemistry ,010402 general chemistry ,01 natural sciences ,Catalysis ,Chemical space ,0104 chemical sciences ,Chemical science ,Computational chemistry ,Excited state ,Reactivity (chemistry) ,Density functional theory - Abstract
Unlike carbonyl compounds, it has long been common understanding that excited imines show virtually no photoreactivity, and hence their properties and potential utility in chemical science remain largely unexplored. Now, a strategy is presented for eliciting latent photoreactivity of imines based on the introduction of a donor-acceptor (D-A) structure to extend the lifetime of their photoexcited states. A series of spectroscopic analyses and density functional theory calculations reveal unique photophysical properties of the D-A-type imines. Furthermore, the reactivity of the D-A-type imines is demonstrated by using them as a photoredox catalyst for atom-transfer radical addition. These findings illuminate a previously neglected chemical space in the field of photochemistry, which will be exploited by taking advantage of the inherent structural modularity of imines.
- Published
- 2019