Issue 6, 2014

Palladium-catalyzed, copper-mediated construction of benzene rings from the reactions of indoles with in situ generated enones

Abstract

Construction of the benzene ring in carbazoles was efficiently realized through a domino dehydrochlorination/alkenylation/cycloaddition–oxidation sequence by means of palladium(II)-catalyzed, copper(II)-mediated reactions of N-protected 2,3-unsubstituted indoles with 3-chloropropiophenones in the presence of a base. 3-Alkenylated indole was confirmed to be formed as the reaction intermediate which then underwent Diels–Alder cycloaddition to the initially in situ generated enone from a 3-chloropropiophenones substrate, and the subsequent dehydrogenative aromatization yielded the carbazole product. The strategy to employ in situ generated enones as the reactive species avoided the use of a large excess of labile substrates and lessened the side reactions.

Graphical abstract: Palladium-catalyzed, copper-mediated construction of benzene rings from the reactions of indoles with in situ generated enones

Supplementary files

Article information

Article type
Research Article
Submitted
25 Apr 2014
Accepted
12 Jun 2014
First published
13 Jun 2014

Org. Chem. Front., 2014,1, 707-711

Author version available

Palladium-catalyzed, copper-mediated construction of benzene rings from the reactions of indoles with in situ generated enones

T. Guo, Q. Jiang, F. Huang, J. Chen and Z. Yu, Org. Chem. Front., 2014, 1, 707 DOI: 10.1039/C4QO00122B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements