Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials , Nanjing Tech University , Nanjing 211816 , China.
Department of Chemistry , University of Science and Technology of China , Hefei , Anhui 230026 , China.
J Org Chem. 2018 Nov 2;83(21):13523-13529. doi: 10.1021/acs.joc.8b01999. Epub 2018 Oct 15.
A scalable and practical synthesis of functionalized indoles via Pd- BuONO cocatalyzed aerobic cycloisomerization of o-allylanilines is reported. Using molecular oxygen as a terminal oxidant, a series of substituted indoles were prepared in moderate to good yields. The avoidance of hazardous oxidants, heavy-metal cocatalysts, and high boiling point solvents such as DMF and DMSO enables this method to be applied in pharmaceutical synthesis. A practical gram-scale synthesis of indomethacin demonstrates its application potential.
本文报道了一种通过 Pd-BuONO 协同催化邻烯丙基苯胺的有氧环化异构化反应来实现功能化吲哚的可规模化、实用的合成方法。该方法以分子氧为末端氧化剂，以中等至良好的收率制备了一系列取代吲哚。由于避免了使用危险的氧化剂、重金属助催化剂以及高沸点溶剂（如 DMF 和 DMSO），该方法可应用于药物合成。吲哚美辛的实际克级合成实验证明了其应用潜力。
