Simple Arenes as Aryne Synthetic Equivalents via Sulfonium Salt Intermediates

Arynes are ephemeral molecules that are yet to be fully exploited in synthetic strategy because they are often challenging to access. These reactive intermediates participate in a myriad of reactions that conventional chemistry is incapable of, making them extremely useful for the synthesis of important molecules like pharmaceuticals and agrochemicals. While classical approaches for synthesizing arynes employ cheap starting material, extremely harsh reagents are necessary to generate the aryne. In contrast, methods that do not require harsh reaction conditions do require starting material that is exceedingly difficult to synthesize. To access arynes quickly and efficiently, the work described herein aims to use abundant starting material to synthesize arynes in the fewest steps possible and without the need for extensive purification. Aryl sulfonium salts can be accessed in a single step from simple arenes and will generate arynes under basic conditions making them an appealing aryne precursor that bridges the gap between the methods described previously.