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Photo-induced arylation of carbazoles with aryldiazonium salts

“Photo-induced arylation of carbazoles with aryldiazonium salts”

Bumpei Maeda, Genki Mori, Yota Sakakibara, Akiko Yagi, Kei Murakami,* Kenichiro Itami*

Asian J. Org. Chem. 2021, Accepted articles. DOI: 10.1002/ajoc.202100191

Arylcarbazoles have been widely used in materials science as important organic semiconductor molecules. To investigate the electronic and photophysical properties of arylcarbazole with different substitution patterns, facile and straightforward synthesis of arylcarbazole derivatives is sought after. Herein we report on photo‐induced direct arylation reactions of carbazole. Treatment of carbazoles with aryldiazonium salts afforded the arylated carbazole. Although the reaction was not regioselective, C1 and C4‐arylated carbazoles were obtained as the major isomers. When N ‐pyridylcarbazole was employed as the substrate with palladium catalyst, the reaction proceeded selectively at C1 position.

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