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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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Publication details

The article was received on 06 Oct 2015, accepted on 24 Nov 2015 and first published on 25 Nov 2015


Article type: Communication
DOI: 10.1039/C5CC08307A
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Citation: Chem. Commun., 2016,52, 1665-1668

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    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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