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. Arynes are utilized in the syntheses of 1,2‐dihydroquinolines, epoxides, and phenolic ethers involving Diels‐Alder, Johnson‐Corey‐Chaykovsky, and Claisen‐type rearrangement reactions, respectively, through three different domino processes