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Synthesis of N-substituted 4-hydroxynaphthalimides using palladium-catalysed hydroxylation
journal contribution
posted on 2016-03-01, 00:00 authored by Cassandra Fleming, Tim NalderTim Nalder, Egan DoevenEgan Doeven, Colin BarrowColin Barrow, Fred PfefferFred Pfeffer, Trent AshtonSuccessful 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.
History
Journal
Dyes and pigmentsVolume
126Pagination
118 - 120Publisher
ElsevierLocation
Amsterdam, The NetherlandsPublisher DOI
ISSN
0143-7208eISSN
1873-3743Language
engPublication classification
C Journal article; C1 Refereed article in a scholarly journalCopyright notice
2016, ElsevierUsage metrics
Keywords
Science & TechnologyPhysical SciencesTechnologyChemistry, AppliedEngineering, ChemicalMaterials Science, TextilesChemistryEngineeringMaterials SciencePalladiumHydroxylationBuchwald-Hartwig4-Hydroxy-1,8-naphthalimideBiarylphosphineFluorescenceRATIOMETRIC FLUORESCENT-PROBEIMAGING HYDROGEN-SULFIDEARYL HALIDESLIVING CELLS1,8-NAPHTHALIMIDE DERIVATIVESPHENOLSETHERSOrganic Chemistry
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