期刊
SYNTHESIS-STUTTGART
卷 -, 期 10, 页码 1712-1718出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1218709
关键词
flavin; photooxidation; redox chemistry; electron transfer; benzyl protecting group
资金
- Deutsche Forschungsgemeinschaft [GRK 1626]
- Fonds der Chemischen Industrie
- University of Regensburg
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 H2O2 and NH3 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.
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