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

Fleming,CL, Ashton,TD and Pfeffer,FM 2014, Synthesis of 4-amino substituted 1,8-naphthalimide derivatives using palladium-mediated amination, Dyes and pigments, vol. 109, pp. 135-143, doi: 10.1016/j.dyepig.2014.05.006.

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Title Synthesis of 4-amino substituted 1,8-naphthalimide derivatives using palladium-mediated amination
Author(s) Fleming,CL
Ashton,TDORCID iD for Ashton,TD orcid.org/0000-0002-6707-6064
Pfeffer,FMORCID iD for Pfeffer,FM orcid.org/0000-0002-5441-6437
Journal name Dyes and pigments
Volume number 109
Start page 135
End page 143
Total pages 9
Publisher Elsevier
Place of publication Amsterdam, The Netherlands
Publication date 2014-10
ISSN 0143-7208
Keyword(s) 4-Aminonaphthalimide
Amination
Buchwald-Hartwig
Naphthalimide
Palladium
Synthesis
Science & Technology
Physical Sciences
Technology
Chemistry, Applied
Engineering, Chemical
Materials Science, Textiles
Chemistry
Engineering
Materials Science
BUCHWALD-HARTWIG AMINATION
APPENDED NAPHTHALIMIDE
COUPLING REACTIONS
DYES
AGENTS
PH
RECEPTORS
ANHYDRIDE
CHLORIDES
SENSORS
Summary 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.
Language eng
DOI 10.1016/j.dyepig.2014.05.006
Field of Research 030503 Organic Chemical Synthesis
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
ERA Research output type C Journal article
Grant ID none
Copyright notice ©2014, Elsevier
Persistent URL http://hdl.handle.net/10536/DRO/DU:30072081

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