Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, Wisconsin 53201, United States.
Org Lett. 2011 Apr 1;13(7):1634-7. doi: 10.1021/ol200069c. Epub 2011 Mar 1.
Tetraarylethylenes can be sequentially transformed into 9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using 1 and 2 equiv of DDQ, respectively, in CH(2)Cl(2) containing methanesulfonic acid, in excellent yields. Efficient access to substituted dibenzochrysenes from tetraarylethylenes establishes the versatility of this procedure over the existing multistep syntheses of dibenzochrysenes. Moreover, the ready regeneration of DDQ from easily recovered reduced DDQ-H(2) continues to advance the use of DDQ/H(+) for the oxidative C-C bond forming reactions.
四芳基乙烯可以分别使用 1 和 2 当量的 DDQ，在含有甲烷磺酸的 CH(2)Cl(2)中，转化为 9,10-二芳基菲和二苯并[g,p]苝，产率优异。从四芳基乙烯高效制备取代二苯并苝，证明了该方法优于现有的多步合成二苯并苝的方法。此外，容易回收的还原态 DDQ-H(2)可以很容易地再生 DDQ，这也推动了 DDQ/H(+)在氧化 C-C 键形成反应中的应用。
