Controlled friedel-crafts acylation of 3, 6-disubstituted-9H-carbazole

Ting Yu Lee; Ming Che Yeh; Ling Chueh Chang; Chi Wi Ong; Che Yu Lin; Jui-Hsien Huang

doi:10.1002/jccs.201200575

Controlled friedel-crafts acylation of 3, 6-disubstituted-9H-carbazole

Ting Yu Lee, Ming Che Yeh, Ling Chueh Chang, Chi Wi Ong, Che Yu Lin, Jui-Hsien Huang

Department of Chemistry

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Abstract

1, 8-Dicarbonylcarbazoles are important starting materials for various applications, especially for pincer-type ligands. The convenient synthesis of a series of 1, 8-diacyl-3, 6-di-tert-butyl-9H-carbazoles (2) by the direct Friedel-Crafts acylation of 3, 6-di-tert-butyl-9H-carbazole (1) is described. During the reaction, the dealkylation also occurred, and 1, 8-diacetyl-3-tert- butyl-9H-carbazole (4) was isolated as well as characterized by an X-ray diffraction analysis. In addition, the steric bulkiness of the acyl chlorides strongly affects the yields of 1, 8-diacylation of 1.

Original language	English
Pages (from-to)	773-778
Number of pages	6
Journal	Journal of the Chinese Chemical Society
Volume	60
Issue number	7
DOIs	https://doi.org/10.1002/jccs.201200575
Publication status	Published - 2013 Oct 21

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All Science Journal Classification (ASJC) codes

Chemistry(all)

Cite this

Lee, T. Y., Yeh, M. C., Chang, L. C., Ong, C. W., Lin, C. Y., & Huang, J-H. (2013). Controlled friedel-crafts acylation of 3, 6-disubstituted-9H-carbazole. Journal of the Chinese Chemical Society, 60(7), 773-778. https://doi.org/10.1002/jccs.201200575

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abstract = "1, 8-Dicarbonylcarbazoles are important starting materials for various applications, especially for pincer-type ligands. The convenient synthesis of a series of 1, 8-diacyl-3, 6-di-tert-butyl-9H-carbazoles (2) by the direct Friedel-Crafts acylation of 3, 6-di-tert-butyl-9H-carbazole (1) is described. During the reaction, the dealkylation also occurred, and 1, 8-diacetyl-3-tert- butyl-9H-carbazole (4) was isolated as well as characterized by an X-ray diffraction analysis. In addition, the steric bulkiness of the acyl chlorides strongly affects the yields of 1, 8-diacylation of 1.",

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T1 - Controlled friedel-crafts acylation of 3, 6-disubstituted-9H-carbazole

AU - Lee, Ting Yu

AU - Yeh, Ming Che

AU - Chang, Ling Chueh

AU - Ong, Chi Wi

AU - Lin, Che Yu

AU - Huang, Jui-Hsien

PY - 2013/10/21

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N2 - 1, 8-Dicarbonylcarbazoles are important starting materials for various applications, especially for pincer-type ligands. The convenient synthesis of a series of 1, 8-diacyl-3, 6-di-tert-butyl-9H-carbazoles (2) by the direct Friedel-Crafts acylation of 3, 6-di-tert-butyl-9H-carbazole (1) is described. During the reaction, the dealkylation also occurred, and 1, 8-diacetyl-3-tert- butyl-9H-carbazole (4) was isolated as well as characterized by an X-ray diffraction analysis. In addition, the steric bulkiness of the acyl chlorides strongly affects the yields of 1, 8-diacylation of 1.

AB - 1, 8-Dicarbonylcarbazoles are important starting materials for various applications, especially for pincer-type ligands. The convenient synthesis of a series of 1, 8-diacyl-3, 6-di-tert-butyl-9H-carbazoles (2) by the direct Friedel-Crafts acylation of 3, 6-di-tert-butyl-9H-carbazole (1) is described. During the reaction, the dealkylation also occurred, and 1, 8-diacetyl-3-tert- butyl-9H-carbazole (4) was isolated as well as characterized by an X-ray diffraction analysis. In addition, the steric bulkiness of the acyl chlorides strongly affects the yields of 1, 8-diacylation of 1.

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10.1002/jccs.201200575