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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 Ashton
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.

History

Journal

Dyes and pigments

Volume

126

Pagination

118 - 120

Publisher

Elsevier

Location

Amsterdam, The Netherlands

ISSN

0143-7208

eISSN

1873-3743

Language

eng

Publication classification

C Journal article; C1 Refereed article in a scholarly journal

Copyright notice

2016, Elsevier