Work

Synthesis of Tetra- ortho -Methoxylated Azobenzene Photoswitches via Sequential Catalytic C–H Activation and Methoxylation

Year: 2024

Type: article

Abstract: Functionalised tetra-ortho-methoxyazobenzenes have been prepared in a two-step approach based on palladium-catalysed C-H ortho bromination of azobenzenes, followed by copper-catalysed 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-catalysed 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 Synthesis 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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c01554

Authors: Albert Ruiz-Soriano, Lara Lamelza, Elena Pizzamiglio, Xavier Just-Baringo

Institution: Universitat de Barcelona

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Ministerio de Economía y Competitividad, Ministerio de Ciencia e Innovación