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Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses
Author(s) -
Hwu Jih Ru,
Panja Avijit,
Gupta Nitesh K.,
Hu YuChen,
Tan KuiThong,
Lin ChunCheng,
Hwang KuoChu,
Hsu MingHua,
Huang WenChieh,
Tsay ShwuChen
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001499
Subject(s) - aryne , chemistry , nucleophile , claisen rearrangement , organic chemistry , cascade reaction , domino , organic synthesis , combinatorial chemistry , catalysis
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.