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Oxidation and Deprotection of Primary Benzylamines by Visible Light Flavin Photocatalysis
| Content Provider | Scilit |
|---|---|
| Author | König, Burkhard Lechner, Robert |
| Copyright Year | 2010 |
| Description | 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. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0029-1218709.pdf |
| Ending Page | 1718 |
| Page Count | 7 |
| Starting Page | 1712 |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/s-0029-1218709 |
| Journal | Synthesis |
| Issue Number | 10 |
| Volume Number | 2010 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2010-03-26 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry Electron Transfer Benzyl Protecting Group |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
