Mechanochemical generation of aryne

Mechanical force is unique in promoting unusual reaction pathways and especially for the generation ofreactive intermediates sometimes inaccessible to other forms of activation. The mechanochemicalgeneration of reactive species could find application in synthetic and materials chemistry alike. However,the nature of these reactive intermediates has been mostly limited to radicals or carbenes. Here, wepresent a new mechanophore that generates a reactive aryne intermediate upon dissociation ofa benzocyclobutene (BCB) core via a force-promoted retro [2 + 2] cycloaddition.