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Synthesis of N-substituted 4-hydroxynaphthalimides using palladium-catalysed hydroxylation

Fleming, Cassandra L., Nalder, Tim D., Doeven, Egan H., Barrow, Colin J., Pfeffer, Frederick M. and Ashton, Trent D. 2016, Synthesis of N-substituted 4-hydroxynaphthalimides using palladium-catalysed hydroxylation, Dyes and pigments, vol. 126, pp. 118-120.

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Title Synthesis of N-substituted 4-hydroxynaphthalimides using palladium-catalysed hydroxylation
Author(s) Fleming, Cassandra L.
Nalder, Tim D.
Doeven, Egan H.ORCID iD for Doeven, Egan H. orcid.org/0000-0003-2677-4269
Barrow, Colin J.ORCID iD for Barrow, Colin J. orcid.org/0000-0002-2153-7267
Pfeffer, Frederick M.ORCID iD for Pfeffer, Frederick M. orcid.org/0000-0002-5441-6437
Ashton, Trent D.ORCID iD for Ashton, Trent D. orcid.org/0000-0002-6707-6064
Journal name Dyes and pigments
Volume number 126
Start page 118
End page 120
Total pages 3
Publisher Elsevier
Place of publication Amsterdam, The Netherlands
Publication date 2016-03
ISSN 0143-7208
1873-3743
Keyword(s) Science & Technology
Physical Sciences
Technology
Chemistry, Applied
Engineering, Chemical
Materials Science, Textiles
Chemistry
Engineering
Materials Science
Palladium
Hydroxylation
Buchwald-Hartwig
4-Hydroxy-1,8-naphthalimide
Biarylphosphine
Fluorescence
RATIOMETRIC FLUORESCENT-PROBE
IMAGING HYDROGEN-SULFIDE
ARYL HALIDES
LIVING CELLS
1,8-NAPHTHALIMIDE DERIVATIVES
PHENOLS
ETHERS
Summary Successful implementation of a palladium-mediated hydroxylation of N-substituted 4-chloro-1,8-naphthalimides has been achieved. The methodology detailed herein utilises 4-chloro-1,8-naphthalic anhydride as a starting point and implements the catalyst/ligand combination of Pd(OAc)2/t-BuXPhos; all of which are relatively inexpensive. A range of imide substituents tolerated the reaction conditions, including acid sensitive substrates which are not compatible with other existing methodology. As such this approach is not only complimentary to existing procedures, it presents a more direct alternative to accessing 4-hydroxy-1,8-naphthalimides.
Language eng
Field of Research 030503 Organic Chemical Synthesis
030107 Sensor Technology (Chemical aspects)
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
Copyright notice ©2016, Elsevier
Persistent URL http://hdl.handle.net/10536/DRO/DU:30082386

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Created: Mon, 21 Mar 2016, 13:44:27 EST

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