%0 Journal Article %1 Shoyama_2018 %A Shoyama, Kazutaka %A Mahl, Magnus %A Seifert, Sabine %A Würthner, Frank %D 2018 %I American Chemical Society (ACS) %J The Journal of Organic Chemistry %K afm cells molecular myown organic %N 10 %P 5339--5346 %R 10.1021/acs.joc.8b00301 %T A General Synthetic Route to Polycyclic Aromatic Dicarboximides by Palladium-Catalyzed Annulation Reaction %U https://doi.org/10.1021%2Facs.joc.8b00301 %V 83 %X 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.

@article{Shoyama_2018, 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.}, added-at = {2018-05-23T09:02:56.000+0200}, author = {Shoyama, Kazutaka and Mahl, Magnus and Seifert, Sabine and Würthner, Frank}, biburl = {https://www.bibsonomy.org/bibtex/24fc79a93c140835e9b104772a422063f/wuerthner_group}, doi = {10.1021/acs.joc.8b00301}, interhash = {f51e54c7b03e1f00188baabfcaee4311}, intrahash = {4fc79a93c140835e9b104772a422063f}, journal = {The Journal of Organic Chemistry}, keywords = {afm cells molecular myown organic}, month = {March}, number = 10, pages = {5339--5346}, publisher = {American Chemical Society (ACS)}, timestamp = {2019-03-11T13:41:25.000+0100}, title = {A General Synthetic Route to Polycyclic Aromatic Dicarboximides by Palladium-Catalyzed Annulation Reaction}, url = {https://doi.org/10.1021%2Facs.joc.8b00301}, volume = 83, year = 2018 }