Wang Zhuo, Liu Yahu A, Yang Hui, Hu Wei-Bo, Wen Ke
Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201210, China.
School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China.
Org Lett. 2022 Mar 11;24(9):1822-1826. doi: 10.1021/acs.orglett.2c00272. Epub 2022 Feb 28.
Despite the fact that the rim and lateral functionalizations of pillar[]arenes have been well explored, -functionalization has rarely been realized. In this work, we report a facile method of introducing a single functionality to the hydroxyl group in A1/A2-dihydroxypillar[5]arene via a Grignard addition to pillar[4]arene[1]quinone followed by a dienone-phenol rearrangement. The described -alkylation/arylation method allowed formation of various mono -alkyl/aryl-substituted A1/A2-dihydroxypillar[5]arenes previously difficult to obtain.
尽管柱芳烃的边缘和侧向功能化已得到充分研究，但γ-功能化却很少实现。在这项工作中，我们报道了一种简便的方法，通过格氏试剂加成到柱[4]芳烃[1]醌上，然后进行双烯酮-酚重排，将单一官能团引入到A1/A2-二羟基柱[5]芳烃的羟基上。所描述的γ-烷基化/芳基化方法能够形成各种以前难以获得的单烷基/芳基取代的A1/A2-二羟基柱[5]芳烃。
