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Synthesis of 4-amino substituted 1,8-naphthalimide derivatives using palladium-mediated amination

journal contribution
posted on 2014-10-01, 00:00 authored by Cassandra Fleming, Trent Ashton, Fred PfefferFred Pfeffer
Successful amination of 4-bromo-1,8-naphthalimides with 'lengthy' imide N-functionality has been achieved using a general palladium mediated approach (conventional thermal protocols were sub-optimal). Only readily available Pd/ligand combinations were considered and the resulting Buchwald-Hartwig procedure using Pd2(dba)3, Xantphos and Cs 2CO3 is high yielding, relatively mild (40-80 °C, 24 h, yields 50-90%), requires only a modest excess of amine (3.0 equiv) and works equally well with other imide N-substituents. As such, the protocol complements existing methods but is superior for more complex substrates. Herein we compare this Pd mediated approach to the methods most commonly used and further demonstrate its utility by synthesising a number of new, highly fluorescent, 4-aminonaphthalimides. © 2014 Elsevier Ltd. All rights reserved.

History

Journal

Dyes and pigments

Volume

109

Pagination

135 - 143

Publisher

Elsevier

Location

Amsterdam, The Netherlands

ISSN

0143-7208

Language

eng

Publication classification

C Journal article; C1 Refereed article in a scholarly journal

Copyright notice

2014, Elsevier