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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Versatile Metal-Free Arylation of BODIPY and Bis(BF2) Chromophores by Using Arylazosulfones in a Sunflow System
Shaiani Maria Gil de Melo1, Thiago Dos Santos1,2, Daniel Gedder Silva1,2
1Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo (FCFRP-USP), Av. do Café, s/n° - Campus Universitário da USP, 14040-903, Ribeirão Preto/SP, Brazil.
Abstract:
BODIPYs have a well-established role in biological sciences as chemosensors and versatile biological markers due to their chemical reactivity, which allows for fine-tuning of their photophysical characteristics. In this work, we combined the unique reactivity of arylazo sulfones with the advantages of a "sunflow" reactor to develop a fast, efficient, and versatile method for the photochemical arylation of BODIPYs and other chromophores. This approach resulted in red-shifted emitting fluorophores due to extended electronic delocalization at the 3- and 5-positions of the BODIPY core. This method represents an advantageous approach for BODIPY functionalization compared to existing strategies.
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