Kawade Rahul Kisan, Hu Chaowei, Dos Santos Nikolas R, Watson Noelle, Lin Xinsong, Hanson Kenneth, Alabugin Igor V
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL, 32306-4390, USA.
Angew Chem Int Ed Engl. 2020 Aug 17;59(34):14352-14357. doi: 10.1002/anie.202006087. Epub 2020 Jul 15.
3-Point annulations, or phenalenannulations, transform a benzene ring directly into a substituted pyrene by "wrapping" two new cycles around the perimeter of the central ring at three consecutive carbon atoms. This efficient, modular, and general method for π-extension opens access to non-symmetric pyrenes and their expanded analogues. Potentially, this approach can convert any aromatic ring bearing a -CH Br or a -CHO group into a pyrene moiety. Depending upon the workup choices, the process can be directed towards either tin- or iodo-substituted product formation, giving complementary choices for further various cross-coupling reactions. The two-directional bis-double annulation adds two new polyaromatic extensions with a total of six new aromatic rings at a central core.
三点环化，即菲并环化，通过在中心环的三个连续碳原子周围“包裹”两个新环，将苯环直接转化为取代芘。这种高效、模块化且通用的π-扩展方法为不对称芘及其扩展类似物的合成开辟了道路。该方法有可能将任何带有-CH₂Br或-CHO基团的芳香环转化为芘部分。根据后处理的选择，该过程可以导向形成锡取代或碘取代的产物，为进一步的各种交叉偶联反应提供了互补的选择。双向双环化在中心核心处添加了两个新的多芳族扩展结构，总共六个新的芳香环。
