In conclusion, we have described a formal dehydrogenation of arenes to generate aryne intermediates. This strategy uses a thianthrenium activating group and is characterized by mild conditions so that valuable halide substituents are retained on the arene and aryne formation occurs at a remote site to the halide. Additionally, nitriles, ketones, esters, pyridine, and terminal alkynes are compatible in this reaction, and aryne formation on clofibrate 1t demonstrates that this is a viable late-stage functionalization technique. The aryne intermediates in this reaction offer opportunities for diversification with a variety of different arynophiles and complementary site-selectivity to other methods. We are continuing to explore the factors that control selectivity of nucleophilic addition to multi-substituted arynes and synthetic opportunities possible by applying aryne logic via formal dehydrogenation of simple arenes.