Catalytic generation of arynes and trapping by nucleophilic addition and iodination

Abstract

A fair exchange: in the title reaction, alkynyllithium serves as an initiator for benzyne generation through an iodine-lithium exchange. When performed in the presence of stoichiometric amounts of a nucleophile, the generated benzyne undergoes attack by lithio nucleophiles to generate aryllithium, which is then iodinated by iodoalkyne to give the iodoarenes 1.