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

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.