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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Lang, Xianjun Zhao, Yubao Ma, Wanhong Ji, Hongwei Zhao, Jincai Chen, Chuncheng |
| Description | Author Affiliation: Lang X ( Key Laboratory of Photochemistry, Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, PR China.) |
| Abstract | Imines are important intermediates for the synthesis of fine chemicals, pharmaceuticals, and agricultural chemicals. Selective oxidation of amines into their corresponding imines with dioxygen is one of the most-fundamental chemical transformations. Herein, we report the oxidation of a series of benzylic amines into their corresponding imines with atmospheric dioxygen as the oxidant on a surface of anatase $TiO_{2}$ under visible-light irradiation (λ>420 nm). The visible-light response of this system was caused by the formation of a surface complex through the adsorption of a benzylic amine onto the surface of $TiO_{2}.$ From the analysis of products of specially designed benzylic amines, we demonstrated that a highly selective oxygenation reaction proceeds via an oxygen-transfer mechanism to afford the corresponding carbonyl compound, whose further condensation with an amine would generate the final imine product. We found that when primary benzylic amines (13 examples), were chosen as the substrates, moderate to excellent selectivities for the imine products were achieved (ca. 38–94 %) in moderate to excellent conversion rates (ca. 44–95 %). When secondary benzylic amines (15 examples) were chosen as the substrates, both the corresponding imines and aldehydes were detected as the main products with moderate to high conversion rates (ca. 18–100 %) and lower selectivities for the imine products (ca. 14–69 %). When tribenzylamine was chosen as the substrate, imine (27 %), dibenzylamine (24 %), and benzaldehyde products (39 %) were obtained in a conversion of 50 %. This report can be viewed as a prototypical system for the activation of CH bonds adjacent to heteroatoms such as N, O, and S atoms, and oxofuctionalization with air or dioxygen as the terminal oxidant under visible-light irradiation using $TiO_{2}$ as the photocatalyst. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 9 |
| Volume Number | 18 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2012-02-27 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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