Kashyap Suraj, Singh Bharat, Ghorai Manas K
Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India.
J Org Chem. 2024 Aug 16;89(16):11429-11445. doi: 10.1021/acs.joc.4c01101. Epub 2024 Aug 1.
A transition metal-free, atom-economical, and highly stereospecific synthetic approach to Friedel-Crafts-type alkylation of arenes/heteroarenes has been developed. The protocol involves the catalytic aminium radical-cation salt (Magic Blue)-initiated S2-type nucleophilic ring opening of activated aziridines with arenes/heteroarenes to give the corresponding 2,2-diarylethylamines up to 99% yield and 85% ee (for nonracemic aziridines) in a very short reaction time. Moreover, on reaction with 1,3-dimethylindole and benzofuran, aziridines undergo domino-ring-opening cyclization (DROC) to give the various biologically significant heterocyclic scaffolds in moderate to good yields.
已开发出一种无过渡金属、原子经济且具有高度立体特异性的合成方法，用于芳烃/杂芳烃的傅克型烷基化反应。该方法包括催化铵自由基阳离子盐（魔蓝）引发的活化氮丙啶与芳烃/杂芳烃的S2型亲核开环反应，在非常短的反应时间内，以高达99%的产率和85%的对映体过量（对于非外消旋氮丙啶）得到相应的2,2-二芳基乙胺。此外，氮丙啶与1,3-二甲基吲哚和苯并呋喃反应时，会发生多米诺开环环化反应（DROC），以中等至良好的产率得到各种具有重要生物学意义的杂环骨架。
