A General Synthetic Route to Polycyclic Aromatic Dicarboximides by Palladium-Catalyzed Annulation Reaction

The Journal of Organic Chemistry
Kazutaka ShoyamaFrank Würthner

Abstract

Here we report a general method for the synthesis of polycyclic aromatic dicarboximides (PADIs) by palladium-catalyzed annulation of naphthalene dicarboximide to different types of aromatic substrates. Reaction conditions were optimized by systematic variation of ligand, solvent, and additive. It was shown that solvent has a decisive effect on the yield of the reaction products, and thus 1-chloronaphthalene as solvent afforded the highest yield. By applying the optimized reaction conditions, a broad series of planar carbo- and heterocycle containing PADIs were synthesized in up to 97% yield. Moreover, this approach could be applied to curved aromatic scaffold to achieve the respective bowl-shaped PADI. Two-fold annulation was accomplished by employing arene diboronic esters, affording polycyclic aromatic bis(dicarboximides). The optical and electrochemical properties of this broad series of PADIs were explored as well.

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Citations

Oct 6, 2018·Chemical Communications : Chem Comm·Lei LiMei-Jin Lin
Jan 11, 2020·ChemistryOpen·Rebecca RennerFrank Würthner
May 23, 2020·Angewandte Chemie·Bartłomiej PigulskiFrank Würthner
Nov 21, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Aneta KurpanikStanisław Krompiec
Aug 6, 2019·Journal of the American Chemical Society·Kazutaka Shoyama, Frank Würthner
Nov 5, 2019·The Journal of Organic Chemistry·Kazutaka ShoyamaFrank Würthner

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