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Issue 8, 2016
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From insertion to multicomponent coupling: temperature dependent reactions of arynes with aliphatic alcohols

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Abstract

The temperature dependent selectivity switch in the reaction of arynes with aliphatic alcohols in THF has been reported. At −20 °C, arynes smoothly insert into the O–H bond of alcohols to form alkyl aryl ethers. Interestingly, at 60 °C, a highly selective multicomponent coupling occurs with the solvent THF acting as the nucleophilic trigger affording (4-(alkoxy)butoxy)arenes.

Graphical abstract: From insertion to multicomponent coupling: temperature dependent reactions of arynes with aliphatic alcohols

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Supplementary files

Article information


Submitted
06 Oct 2015
Accepted
24 Nov 2015
First published
25 Nov 2015

Chem. Commun., 2016,52, 1665-1668
Article type
Communication
Author version available

From insertion to multicomponent coupling: temperature dependent reactions of arynes with aliphatic alcohols

M. Thangaraj, S. S. Bhojgude, M. V. Mane and A. T. Biju, Chem. Commun., 2016, 52, 1665
DOI: 10.1039/C5CC08307A

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