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From insertion to multicomponent coupling: temperature dependent reactions of arynes with aliphatic alcohols
Journal article   Peer reviewed

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

Manikandan Thangaraj, Sachin Suresh Bhojgude, Manoj V. Mane and Akkattu T. Biju
Chemical communications (Cambridge, England), Vol.52(8), pp.1665-1668
01/01/2016
DOI: https://doi.org/10.1039/c5cc08307a
PMID: 26658297

Abstract

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

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