Organic Chemistry Division, ‡Physical and Materials Chemistry Division, and §Center for Materials Characterization, CSIR-National Chemical Laboratory (CSIR-NCL) , Dr. Homi Bhabha Road, Pune 411008, India.
J Org Chem. 2014 May 16;79(10):4757-62. doi: 10.1021/jo500819w. Epub 2014 May 2.
A new procedure for the mild, practical, and scalable Diels-Alder reaction of tropones with arynes is reported. Differently substituted tropones undergo selective [4 + 2] cycloaddition with arynes generated in situ by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates, allowing the formation of functionalized benzobicyclo[3.2.2]nonatrienone derivatives in moderate to good yields. In addition, the photophysical properties of the cycloadducts are presented.
报道了一种温和、实用且可规模化的新型托品酮与芳炔的 Diels-Alder 反应方法。不同取代的托品酮与通过氟化物诱导的 2-(三甲基甲硅烷基)芳基三氟甲磺酸酯的 1,2-消除原位生成的芳炔发生选择性[4+2]环加成反应，以中等至良好的收率生成官能化的苯并双环[3.2.2]壬三烯酮衍生物。此外，还介绍了环加成产物的光物理性质。
