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Issue 2, 2015
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Indium-catalyzed intramolecular hydroarylation of aryl propargyl ethers

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Abstract

Indium(III) halides catalyze efficiently the intramolecular hydroarylation (IMHA) of aryl propargyl ethers. The reaction proceeds regioselectively with terminal and internal alkynes bearing electron-rich and electron-deficient substituents in the benzenes and alkynes affording only the 6-endo dig cyclization product. Additionally, a sequential indium-catalyzed IMHA and palladium-catalyzed Sonogashira coupling can be performed in one reaction vessel. Experiments with deuterium support a mechanism through electrophilic aromatic substitution.

Graphical abstract: Indium-catalyzed intramolecular hydroarylation of aryl propargyl ethers

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Supplementary files

Article information


Submitted
24 Sep 2014
Accepted
21 Oct 2014
First published
22 Oct 2014

Org. Biomol. Chem., 2015,13, 379-387
Article type
Paper
Author version available

Indium-catalyzed intramolecular hydroarylation of aryl propargyl ethers

L. Alonso-Marañón, M. M. Martínez, L. A. Sarandeses and J. P. Sestelo, Org. Biomol. Chem., 2015, 13, 379
DOI: 10.1039/C4OB02033B

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