Pan Xiaoguang, Wang Zehua, Kan Linglong, Mao Ying, Zhu Yasheng, Liu Lei
School of Pharmaceutical Sciences, Shandong University Jinan 250012 China
School of Chemistry and Chemical Engineering, Shandong University Jinan 250100 China.
Chem Sci. 2020 Jan 29;11(9):2414-2419. doi: 10.1039/c9sc05894j.
A cross-dehydrogenative coupling strategy for enantioselective access to acyclic CF-substituted all-carbon quaternary stereocenters has been established. By using catalytic DDQ with MnO as an inexpensive terminal oxidant, asymmetric cross coupling of racemic δ-CF-substituted phenols with indoles proceeded smoothly, providing CF-bearing all-carbon quaternary stereocenters with excellent chemo- and enantioselectivities. The generality of the strategy is further demonstrated by efficient construction of all-carbon quaternary stereocenters bearing other polyfluoroalkyl and perfluoroalkyl groups such as CFCl, CF, and CF.
一种对映选择性构建无环CF取代全碳季碳立体中心的交叉脱氢偶联策略已被确立。通过使用催化量的DDQ并以MnO作为廉价的终端氧化剂，外消旋δ-CF取代苯酚与吲哚的不对称交叉偶联反应顺利进行，以优异的化学选择性和对映选择性提供了含CF的全碳季碳立体中心。该策略的通用性通过高效构建带有其他多氟烷基和全氟烷基（如CFCl、CF和CF）的全碳季碳立体中心得到进一步证明。
