Core-substituted naphthalenediimides (cNDIs) are a class of electron-poor aromatic compounds that have undergone a recent surge in popularity due to their potential use in a variety of research areas and applications. Synthesis of the majority of cNDI compounds goes through key bromo-substituted NDI intermediates, and while there have been advances in the synthesis of bis-substituted diBr-NDI, the related single substituted Br-NDI has remained notoriously difficult to synthesize in even modest yields. Discussed here is new methodology for the efficient synthesis of mono-core functionalized Br-NDI derivatives. The single-site core-substituted 1,4,5,8-naphthalene anhydride is achieved using Cu/N-bromosuccinimide in strongly acidic conditions with significant evidence for a mechanism involving Cu-mediated oxidative C-H incretion. The details of this reaction and its mechanism will be discussed.

Selective synthesis of mono-functionalized naphthalenediimideds by copper-catalyzed C-H activation

2019 Spring National Meeting

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