Department of Chemistry, Indian Institute of Technology, Kanpur, Uttar Pradesh 208016, India.
School of Chemistry, Indian Institute of Science Education and Research, Thiruvananthapuram 695551, India.
J Org Chem. 2023 May 5;88(9):5431-5439. doi: 10.1021/acs.joc.2c03059. Epub 2023 Apr 24.
Visible light-mediated facile synthesis of heteroarenes, namely, isoquinolines, benzothiazoles, and quinazolines, is demonstrated by employing isocyanides and inexpensive acyl peroxides. It is shown for the first time that singlet-excited isocyanides decompose acyl peroxides into aryl/alkyl radicals. The latter attack isocyanides, yielding imidoyl radicals that subsequently cyclize to afford heteroarene products. The protocol involving radical cascade reactions obviates the requirement of any external photocatalyst, oxidant, additive, and base.
可见光介导的简便合成杂芳烃，即异喹啉、苯并噻唑和喹唑啉，通过使用异氰化物和廉价的过氧酰基来实现。首次表明，单重激发态异氰化物将过氧酰基分解为芳基/烷基自由基。后者攻击异氰化物，生成酰基自由基，然后环化得到杂芳烃产物。该反应涉及自由基级联反应，无需任何外部光催化剂、氧化剂、添加剂和碱。
