Myriad Aryne Derivatives from Carboxylic Acids - Nature

"Densely substituted aromatic rings are ubiquitous in pharmaceuticals and agrochemicals 1. For making aromatic molecules, aryne intermediates have synthetic potential that rivals most functional groups 2. They readily react with nucleophiles, participate in pericyclic reactions, and activate inert σ-bonds. Despite their potential, arynes are currently used by a specialized community for mainly niche applications. The lack of widespread adoption of arynes is due to the undesirable means to generate them."

"Readily available carboxylic acids are derivatized in a single step to a make a precursor which is then activated by blue light or by heat. Dozens of previously unknown aminated arynes, including pyridynes, are generated in this work, opening the door to drug discovery using aryne intermediates. We envision that future development of this precursor platform will allow even more decorated arynes to be accessed, further expanding the reach of aryne chemistry."

Densely substituted aromatic rings are common in pharmaceuticals and agrochemicals. Aryne intermediates react with nucleophiles, participate in pericyclic reactions, and activate inert σ-bonds. Current aryne use is limited by undesirable generation methods and niche adoption. A designed aryne precursor enables single-step derivatization of readily available carboxylic acids. The precursor can be activated by blue light or heat to form arynes. Dozens of previously unknown aminated arynes, including pyridynes, were generated. The new precursor platform enables access to decorated arynes and opens opportunities for drug discovery and broader application of aryne chemistry.

Read at Nature