Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses

Synthetic application of arynes is broadened by their reactions with neutral N ‐, S ‐, and O ‐containing nucleophiles to produce three types of compounds. Accordingly, 1,2‐dihydroquinolines are synthesized from Schiff bases, alkynes, and arynes through a Diels‐Alder reaction. Epoxides are prepared from thioethers and arynes along with aldehydes or ketones through a Johnson‐Corey‐Chaykovsky reaction. Phenolic ethers are produced from allyl ethers and arynes through a Claisen‐type rearrangement. These target molecules, including natural products γ‐asarone, asaricin, and a cholesteryl phenolic ether, are formed through reactions initiated by arynes. These new reactions share a prevailing feature of domino processes, which are carried out in a single flask and afford the desired products in good to high yields.