On the use of 2-(trimethylsilyl)iodobenzene as a benzyne precursor

A mild method for the generation of benzynes from 2-(trimethylsilyl)iodobenzene derivatives is reported. The employment of silver fluoride in conjunction with caesium fluoride is key for promoting useful levels of elimination and providing benzyne derived products in good yields. Moreover, the substrates are accessed by a novel alkynyl iodide cycloaddition.