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Pyrene-based D-A Molecules as Efficient Heterogeneous Catalysts for Visible-Light-Induced Aerobic Organic Transformations.

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In this work, we described an efficient visible light promoted aerobic dehydro-coupling of amines, oxidation of thioethers and hydroxylation of arylboronic acids under benign conditions by using pyrene-based donor-acceptor (D-A)… Click to show full abstract

In this work, we described an efficient visible light promoted aerobic dehydro-coupling of amines, oxidation of thioethers and hydroxylation of arylboronic acids under benign conditions by using pyrene-based donor-acceptor (D-A) conjugated organic molecules. Donor-acceptor structure influences their π-conjugation and band gap a lot, and thereby enhanced their visible light absorption ability, single electron transfer and oxidative behaviors. Alkynyl units in PS-IV play a crucial role in the catalyst which could serve as electron transferring bridge to strength electron delocalization, and thus facilitate the single electron transfer from photosensitizer to substrates, thus make it an efficient ·O2- generator. While PS-III without alkynyl units tends to produce 1O2. Therefore, these molecules can serve as efficient catalysts for different kinds of visible-light-induced aerobic organic reactions. More importantly, the simply structured molecule is insoluble and stable in various solvents, and thus could be recycled as heterogeneous catalyst for many rounds with slight catalytic activity degradation. Large scale (1 mol) reaction of benzylamine coupling proceeded smoothly under the standard conditions.

Keywords: light induced; induced aerobic; pyrene based; visible light; aerobic organic

Journal Title: ChemSusChem
Year Published: 2022

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