Vidyasagar, Adiyala and Shi, Jinwei and Kreitmeier, Peter and Reiser, Oliver (2018) Bromo- or Methoxy-Group-Promoted Umpolung Electron Transfer Enabled, Visible-Light-Mediated Synthesis of 2-Substituted Indole-3-glyoxylates. ORGANIC LETTERS, 20 (22). pp. 6984-6989. ISSN 1523-7060, 1523-7052
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A visible-light-mediated radical tandem cyclization of ortho-isocyano-alpha-bromo cinnamates to 2-substituted indole-3-glyoxylates is achieved by formation of both C-C/C-S and C-O bonds. The reaction proceeds through a hitherto unprecedented bromine- or methoxy-group-promoted umpolung back electron transfer from an a-carbonyl radical to the photocatalyst. This method allows preparation of diverse 2-arylated or 2-thioarylated indole-3-glyoxylates. The glyoxylate group installed in the products can be utilized for several biologically relevant manipulations.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | DEPENDENT KINASE INHIBITORS; SIMPLE INDOLE ALKALOIDS; C-H ARYLATION; 2,3-DISUBSTITUTED INDOLES; BIOLOGICAL EVALUATION; PHOTOREDOX CATALYSIS; ALPHA-BROMOCHALCONES; METAL-FREE; CYCLIZATION; DERIVATIVES; |
| 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: | 09 Oct 2019 06:40 |
| Last Modified: | 09 Oct 2019 06:40 |
| URI: | https://pred.uni-regensburg.de/id/eprint/13535 |
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