Synthesis of N-substituted 4-hydroxynaphthalimides using palladium-catalysed hydroxylation. (March 2016)

• Record Type: Journal Article
• Authors: Fleming, Cassandra L.; Nalder, Tim D.; Doeven, Egan H.; Barrow, Colin J.; Pfeffer, Frederick M.; Ashton, Trent D.
• Is Part Of: Dyes and pigments. Volume 126(2016)
• Page Start: 118
• Page End: 120
• Publication Date: 2016-03
• Subjects: Palladium -- Hydroxylation -- Buchwald-Hartwig -- 4-Hydroxy-1, 8-naphthalimide -- Biarylphosphine -- Fluorescence; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2015.11.007
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: 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. Graphical abstract: Highlights: Palladium-mediated access to 4-hydroxy-1, 8-naphthalimides from 4-chloro derivatives. The methodology employs cheap and readily available substrates and reagents. Acid labile functional groups are tolerated.