Modular Synthesis of Carbazole-Substituted Phthalimides as Potential Photocatalysts

This paper is dedicated to the memory of Professor Ferenc Fülöp.

Abstract

The modular synthesis of carbazole functionalized phthalimides (PIs) and their applicability as catalyst in selected photocatalytic transformations are reported. The developed synthetic approach provides high variability of phthalimide considering that the synthesis of the phthalimide core can be easily performed. Starting from fluorophthalic acid anhydrides, the corresponding fluorophthalimides were prepared with various amines, and the fluoro function ensured the introduction of carbazoles into the phthalimide framework through aromatic nucleophilic substitution. Besides the synthetic developments, some of the carbazolyl phthalimides were tested in four different photocatalytic transformations, which showed attractive and comparable activity to the known 4-CzIPN and noble metal complexes.

Key words

carbazoles - heterocycles - modular synthesis - photocatalysis - phthalimides

Publication History

Received: 23 July 2021

Accepted after revision: 17 September 2021

Accepted Manuscript online:
17 September 2021

Article published online:
10 November 2021

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