Issue 2, 2015

Indium-catalyzed intramolecular hydroarylation of aryl propargyl ethers

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

Supplementary files

Article information

Article type
Paper
Submitted
24 Sep 2014
Accepted
21 Oct 2014
First published
22 Oct 2014

Org. Biomol. Chem., 2015,13, 379-387

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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