Hossain, Asik and Vidyasagar, Adiyala and Eichinger, Christian and Lankes, Christian and Phan, Jenny and Rehbein, Julia and Reiser, Oliver (2018) Visible-Light-Accelerated Copper(II)-Catalyzed Regio- and Chemoselective Oxo-Azidation of Vinyl Arenes. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 57 (27). pp. 8288-8292. ISSN 1433-7851, 1521-3773
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The visible-light-accelerated oxo-azidation of vinyl arenes with trimethylsilylazide and molecular oxygen as stoichiometric oxidant was achieved. In contrast to photocatalysts based on iridium, ruthenium, or organic dyes, [Cu(dap)(2)]Cl or [Cu(dap)Cl-2] were found to be unique for this transformation, which is attributed to their ability to interact with the substrates through ligand exchange and rebound mechanisms. Cu-II is proposed as the catalytically active species, which upon coordinating azide will undergo light-accelerated homolysis to form Cu-I and azide radicals. This activation principle (Cu-II-XCuI+X-.) opens up new avenues for copper-based photocatalysis.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | TRANSFER RADICAL-ADDITION; ALPHA-AZIDO KETONES; COPPER PHOTOREDOX CATALYST; FACILE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; PHENACYL THIOCYANATES; TRIMETHYLSILYL AZIDE; ORGANIC-SYNTHESIS; DOUBLE-BONDS; ALKENES; copper; homogeneous Catalysis; oxo-azidation; oxygen; photocatalysis |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 23 Mar 2020 07:46 |
| Last Modified: | 06 Apr 2020 05:09 |
| URI: | https://pred.uni-regensburg.de/id/eprint/14265 |
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