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

Research output: Contribution to journalArticle

1 Citation (Scopus)

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 languageEnglish
Pages (from-to)773-778
Number of pages6
JournalJournal of the Chinese Chemical Society
Volume60
Issue number7
DOIs
Publication statusPublished - 2013 Oct 21

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Acylation
Diacetyl
X ray diffraction analysis
Chlorides
Ligands
carbazole

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Lee, Ting Yu ; Yeh, Ming Che ; Chang, Ling Chueh ; Ong, Chi Wi ; Lin, Che Yu ; Huang, Jui-Hsien. / Controlled friedel-crafts acylation of 3, 6-disubstituted-9H-carbazole. In: Journal of the Chinese Chemical Society. 2013 ; Vol. 60, No. 7. pp. 773-778.
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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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Controlled friedel-crafts acylation of 3, 6-disubstituted-9H-carbazole. / Lee, Ting Yu; Yeh, Ming Che; Chang, Ling Chueh; Ong, Chi Wi; Lin, Che Yu; Huang, Jui-Hsien.

In: Journal of the Chinese Chemical Society, Vol. 60, No. 7, 21.10.2013, p. 773-778.

Research output: Contribution to journalArticle

TY - JOUR

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

AU - Lee, Ting Yu

AU - Yeh, Ming Che

AU - Chang, Ling Chueh

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AU - Lin, Che Yu

AU - Huang, Jui-Hsien

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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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