Dearomatization_re-revised 2.pdf (737.01 kB)
Download fileReactivity of Arynes for Arene Dearomatization
journal contribution
posted on 2019-01-14, 00:00 authored by Rajdip Karmakar, Anh Le, Peipei Xie, Yuanzhi Xia, Daesung LeeAn unprecedented aryne-mediated dearomatization reaction is described. An aryne intermediate generated from arenesulfonyl ynamide-tethered tri- and tetraynes reacts with both the π-systems of a tethered alkene and the arenesulfonyl group to generate cyclohexa-1,3-diene-containing penta- and hexacyclic frameworks. DFT-calculations show a nucleophilic dearomatization mechanism involving a zwitterionic intermediate derived from an aryne. A novel halogen effect on the efficiency of the dearomatization and deterrence of aromatization of the cyclohexa-1,3-diene moiety was also observed