4.6 Article

Visible-light-Induced synthesis of imidazolidines through formal [3+2] cycloaddition of aromatic imines with N,N,N', N'-tetramethyldiaminomethane

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ELSEVIER SCIENCE SA
DOI: 10.1016/j.jphotochem.2022.114239

Keywords

Nitrogen heterocycles; Cycloaddition; Photo -reaction; Radical reactions; Domino reactions

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In this study, a new method for synthesizing pharmacological drugs using a photosensitizer was proposed. The study showed that imidazolidines can be synthesized through a photocycloaddition reaction under specific conditions. A reaction mechanism was proposed based on quenching experiments, quantum yield, and potential measurements.
Imidazolidine is a saturated heterocycle with a cyclic aminal core that can be used to develop new pharmaco-logical drugs. Heteroleptic cyclometalated Ir(III) complex photosensitizers have been shown to enable the un-precedented synthesis of imidazolidines through a formal [3 + 2] photocycloaddition of aromatic imines with N, N,N',N'-tetramethyldiaminomethane. Herein, a reaction mechanism based on quenching experiments, quantum yield, ground-state redox potentials, and excited-state potentials is proposed.

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