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Issue 44, 2020
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Lewis acid-catalyzed double addition of indoles to ketones: synthesis of bis(indolyl)methanes with all-carbon quaternary centers

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Abstract

We report herein a Lewis acid-catalyzed nucleophilic double-addition of indoles to ketones under mild conditions. This process occurs with various ketones ranging from dialkyl ketones to diaryl ketones, thereby providing access to an array of bis(indolyl)methanes bearing all-carbon quaternary centers, including tetra-aryl carbon centers. The products can be transformed into bis(indole)-fused polycyclics and bis(indolyl)alkenes.

Graphical abstract: Lewis acid-catalyzed double addition of indoles to ketones: synthesis of bis(indolyl)methanes with all-carbon quaternary centers

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Article information


Submitted
17 Sep 2020
Accepted
21 Oct 2020
First published
21 Oct 2020

Org. Biomol. Chem., 2020,18, 9060-9064
Article type
Paper

Lewis acid-catalyzed double addition of indoles to ketones: synthesis of bis(indolyl)methanes with all-carbon quaternary centers

S. O. Lee, J. Choi, S. Kook and S. Y. Lee, Org. Biomol. Chem., 2020, 18, 9060
DOI: 10.1039/D0OB01916J

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