Fluorinated unsymmetrical acridines are efficiently prepared by means of a tandem micellar Buchwald-Hartwig amination followed by an acid-promoted cyclization. The overall process is advantageous with respect to previously described protocols both in terms of efficiency and sustainability. The role of the cosolvent in the amination step is highlighted, demonstrating that rather than resorting to highly expensive catalysts, Buchwald-Hartwig aminations can be straightforwardly carried out by tuning the reaction site polarity.
Vaghi, L., Sanzone, A., Sassi, M., Pagani, S., Papagni, A., Beverina, L. (2018). Synthesis of Fluorinated Acridines via Sequential Micellar Buchwald-Hartwig Amination/Cyclization of Aryl Bromides. SYNTHESIS, 50(8), 1621-1628 [10.1055/s-0036-1591937].
Synthesis of Fluorinated Acridines via Sequential Micellar Buchwald-Hartwig Amination/Cyclization of Aryl Bromides
Vaghi, LucaPrimo
;Sanzone, Alessandro;Sassi, Mauro;Papagni, Antonio;Beverina, Luca
2018
Abstract
Fluorinated unsymmetrical acridines are efficiently prepared by means of a tandem micellar Buchwald-Hartwig amination followed by an acid-promoted cyclization. The overall process is advantageous with respect to previously described protocols both in terms of efficiency and sustainability. The role of the cosolvent in the amination step is highlighted, demonstrating that rather than resorting to highly expensive catalysts, Buchwald-Hartwig aminations can be straightforwardly carried out by tuning the reaction site polarity.
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