Beilstein-Institut Acta Medica Okayama 1860-5397 21 2025 Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra 670 679 EN Yuuki Ishii Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Minoru Yamaji Division of Molecular Science, Graduate School of Science and Engineering, Gunma University Fumito Tani Institute for Materials Chemistry and Engineering, Kyushu University Kenta Goto Institute for Materials Chemistry and Engineering, Kyushu University Yoshihiro Kubozono Research Institute for Interdisciplinary Science, Okayama University Hideki Okamoto Graduate School of Environmental, Life, Natural Science and Technology, Okayama University [n]Phenacenes ([n] = 5-7), octafluorinated at the terminal benzene rings (F8-phenacenes: F8PIC, F8FUL, and F87PHEN), were photochemically synthesized, and their electronic spectra were investigated to reveal the effects of the fluorination on the electronic features of phenacene molecules. F8-Phenacenes were conveniently synthesized by the Mallory photoreaction of the corresponding fluorinated diarylethenes as the key step. Upon fluorination on the phenacene cores, the absorption and fluorescence bands of the F8-phenacenes in CHCl3 systematically red-shifted by ca. 3-5 nm compared to those of the corresponding parent phenacenes. The vibrational progressions of the absorption and fluorescence bands were little affected by the fluorination in the solution phase. In the solid state, the absorption band of F8-phenacenes appeared in the similar wavelength region for the corresponding parent phenacenes whereas their fluorescence bands markedly red-shifted and broadened. These observations suggest that the intermolecular interactions of excited-state F8-phenacene molecules are significantly different from those of the corresponding parent molecules, most likely due to different crystalline packing motifs. No potential conflict of interest relevant to this article was reported.

Beilstein-Institut Acta Medica Okayama 1860-5397 20 2024 Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus Pseudoceratina 3215 3220 EN Shin-Ichiro Kurimoto Faculty of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University Kouta Inoue Showa Pharmaceutical University Taito Ohno Showa Pharmaceutical University Takaaki Kubota Faculty of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University A new psammaplysin derivative, ceratinadin G (1), was obtained from the Okinawan marine sponge Pseudoceratina sp., and the gross structure was clarified through spectroscopic and spectrometric analyses. The absolute configuration of compound 1 was established by comparing its NMR and ECD data with those of the known psammaplysin derivative, psammaplysin F (2). Ceratinadin G (1) is a rare nitrile containing a cyano group as aminoacetonitrile, and is the first psammaplysin derivative possessing a cyano group. In vitro assays indicated that compound 1 displayed moderate cytotoxicity against L1210 murine leukemia cells and KB epidermoid carcinoma cells. No potential conflict of interest relevant to this article was reported.

Beilstein-Institut Acta Medica Okayama 1860-5397 20 2024 Electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines under mild conditions with a proton-exchange membrane reactor 1560 1571 EN Koichi Mitsudo Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Atsushi Osaki Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Haruka Inoue Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Eisuke Sato Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Naoki Shida Graduate School of Engineering Science and Advanced Chemical Energy Research Center, Yokohama National University Mahito Atobe Graduate School of Engineering Science and Advanced Chemical Energy Research Center, Yokohama National University Seiji Suga Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University An electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines using a proton-exchange membrane (PEM) reactor was developed. Cyanoarenes were then reduced to the corresponding benzylamines at room temperature in the presence of ethyl phosphate. The reduction of nitroarenes proceeded at room temperature, and a variety of anilines were obtained. The quinoline reduction was efficiently promoted by adding a catalytic amount of p-toluenesulfonic acid (PTSA) or pyridinium p-toluenesulfonate (PPTS). Pyridine was also reduced to piperidine in the presence of PTSA. No potential conflict of interest relevant to this article was reported.

Beilstein-Institut Acta Medica Okayama 1860-5397 18 2022 Electrochemical hydrogenation of enones using a proton- exchange membrane reactor: selectivity and utility 1055 1061 EN Koichi Mitsudo Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Haruka Inoue Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Yuta Niki Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Eisuke Sato Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Electrochemical hydrogenation of enones using a proton-exchange membrane reactor is described. The reduction of enones proceeded smoothly under mild conditions to afford ketones or alcohols. The reaction occurred chemoselectively with the use of different cathode catalysts (Pd/C or Ir/C). No potential conflict of interest relevant to this article was reported.