Lechner, Robert and Koenig, Burkhard (2010) Oxidation and Deprotection of Primary Benzylamines by Visible Light Flavin Photocatalysis. SYNTHESIS-STUTTGART (10). pp. 1712-1718. ISSN 0039-7881,
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We report a photocatalytic oxidation procedure that can be used to convert benzylamines into their corresponding aldehydes under mild conditions without over-oxidation, using riboflavin tetraacetate as photocatalyst and blue emitting LEDs (440 nm) as light source. Oxygen is the terminal oxidant and H(2)O(2) and NH(3) appear as the only byproducts of the oxidation of primary benzylamines. Furthermore, we have developed a photocatalytic protocol for 4-methoxybenzyl (Mob) group deprotection of primary amines and alcohols. Double bonds, benzyl-protected esters and alcohols are tolerated under the applied conditions, whereas the deprotection of protected secondary amines is not applicable. Mob-protected carboxylic acids and carboxybenzoyl (Cbz) protected amines are inert under the photodeprotection conditions.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PHOTOINDUCED ELECTRON-TRANSFER; MONOAMINE-OXIDASE CATALYSIS; BAEYER-VILLIGER REACTION; HYDROGEN-PEROXIDE; MODEL SYSTEMS; FLAVOENZYME ACTIVITY; MOLECULAR-OXYGEN; AMINO-ACIDS; SENSITIZED PHOTOOXIDATION; REDUCTIVE AMINATION; flavin; photooxidation; redox chemistry; electron transfer; benzyl protecting group |
| 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: | 03 Aug 2020 06:43 |
| Last Modified: | 03 Aug 2020 06:43 |
| URI: | https://pred.uni-regensburg.de/id/eprint/24804 |
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