Synthesis 2018; 50(08): 1621-1628
DOI: 10.1055/s-0036-1591937
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of Fluorinated Acridines via Sequential Micellar Buchwald–Hartwig Amination/Cyclization of Aryl Bromides

Luca Vaghi
a  Department of Materials Science, University of Milano-Bicocca, via R. Cozzi 55, 20125 Milano, Italy
,
Alessandro Sanzone
a  Department of Materials Science, University of Milano-Bicocca, via R. Cozzi 55, 20125 Milano, Italy
,
Mauro Sassi
a  Department of Materials Science, University of Milano-Bicocca, via R. Cozzi 55, 20125 Milano, Italy
b  Department of Materials Science, University of Milano-Bicocca, and INSTM Milano-Bicocca Research Unit, via R. Cozzi 55, 20125 Milano, Italy   Email: luca.beverina@unimib.it
,
Simone Pagani
a  Department of Materials Science, University of Milano-Bicocca, via R. Cozzi 55, 20125 Milano, Italy
,
Antonio Papagni
a  Department of Materials Science, University of Milano-Bicocca, via R. Cozzi 55, 20125 Milano, Italy
,
Luca Beverina*
a  Department of Materials Science, University of Milano-Bicocca, via R. Cozzi 55, 20125 Milano, Italy
b  Department of Materials Science, University of Milano-Bicocca, and INSTM Milano-Bicocca Research Unit, via R. Cozzi 55, 20125 Milano, Italy   Email: luca.beverina@unimib.it
› Author Affiliations
The contribution from CNR through the Progetto Premiale 2012 EOS is gratefully acknowledged.
Further Information

Publication History

Received: 21 December 2017

Accepted after revision: 26 January 2018

Publication Date:
26 February 2018 (online)


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.

Supporting Information

 
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