Carregant...
Fitxers
Tipus de document
ArticleVersió
Versió publicadaData de publicació
Llicència de publicació
Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/220539
Synthesis of Tetra-ortho-Methoxylated Azobenzene Photoswitches via Sequential Catalytic C-H Activation and Methoxylation
Títol de la revista
Director/Tutor
ISSN de la revista
Títol del volum
Recurs relacionat
Resum
Functionalized tetra-ortho-methoxyazobenzenes have been prepared in a two-step approach based on palladium-catalyzed C–H ortho bromination of azobenzenes, followed by copper-catalyzed methoxylation. The method has shown a broad tolerance to different functional groups that could not be incorporated by previous strategies. With this two-step transition metal-catalyzed strategy, we achieved overall yields that range from good to excellent and enable the exploitation of these highly coveted photoswitches. The superior robustness of this scaffold for solid phase peptide synthesis (SPPS) applications when compared to its chlorinated counterpart has been demonstrated after extensive treatments with piperidine while bound to a RinkAmide ChemMatrix resin, showcasing their potential for use in the synthesis of red-light-operated peptides.
Matèries (anglès)
Citació
Citació
RUIZ-SORIANO, Albert, LAMELZA, Lara, PIZZAMIGLIO, Elena, JUST BARINGO, Xavier. Synthesis of Tetra-ortho-Methoxylated Azobenzene Photoswitches via Sequential Catalytic C-H Activation and Methoxylation. _Journal of Organic Chemistry_. 2024. Vol. 89, núm. 23, pàgs. 17141-17146. [consulta: 14 de gener de 2026]. ISSN: 0022-3263. [Disponible a: https://hdl.handle.net/2445/220539]