Wang, Hua and Wang, Shun and George, Vincent and Llorente, Galder and Koenig, Burkhard (2022) Photo-Induced Homologation of Carbonyl Compounds for Iterative Syntheses. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 61 (49). ISSN 1433-7851, 1521-3773
Full text not available from this repository. (Request a copy)Abstract
We describe a photo-induced reaction for the in situ generation of highly reactive alkyl diazo species from carbonyl precursors via photo-excitation of N-tosylhydrazone anions. The diazo intermediates undergo efficient C-H insertion of aldehydes, leading to the productive synthesis of aldehydes and ketones. The method is applicable to the iterative synthesis of densely functionalized carbonyl compounds through sequential trapping of the diazo species with various aldehydes. The reaction proceeds without the need of any catalyst by light irradiation and features high functional group tolerance. More than 70 examples, some performed on a gram-scale, demonstrate the broad applicability of this reaction sequence in synthesis.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | DIAZO-COMPOUNDS; C-H; AUTOMATED SYNTHESIS; ALDEHYDES; KETONES; TOSYLHYDRAZONES; MOLECULES; CHEMISTRY; REAGENTS; ACIDS; Buchner-Curtius-Schlotterbeck Reaction; Carbonyl Homologation; Diazo Compounds; Hydrazone; Photochemistry |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 09 Jan 2024 09:31 |
| Last Modified: | 09 Jan 2024 09:31 |
| URI: | https://pred.uni-regensburg.de/id/eprint/57101 |
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