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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Synthesis of carbazole-based hetero-core-modified porphyrins
Chihiro Maeda1, Motoki Masuda, Naoki Yoshioka
1Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Kohoku-ku, Yokohama 223-8522, Japan.
Abstract:
Cu(I)-mediated annulation reaction of a 1,1'-(1,3-butadiyne)-8,8'-(2,5-thiophene)-bridged carbazole dimer 10 with amines provided the N-substituted carbazole-based isophlorines 11a-11c. A similar annulation reaction with selenium in the presence of hydrazine monohydrate afforded hetero-core-modified isophlorine 12. The oxidation of 12 generated the corresponding 21-selena-23-thiaporphyrin 13, which exhibited NIR absorption. The intramolecular charge transfer from Se to S was confirmed by the (1)H NMR results along with DFT calculations.
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