Title | From alkylarenes to anilines via site-directed carbon-carbon amination |
Authors | Liu, Jianzhong Qiu, Xu Huang, Xiaoqiang Luo, Xiao Zhang, Cheng Wei, Jialiang Pan, Jun Liang, Yujie Zhu, Yuchao Qin, Qixue Song, Song Jiao, Ning |
Affiliation | Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing, Peoples R China Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai, Peoples R China |
Issue Date | 2019 |
Publisher | NATURE CHEMISTRY |
Abstract | Anilines are fundamental motifs in various chemical contexts, and are widely used in the industrial production of fine chemicals, polymers, agrochemicals and pharmaceuticals. A recent development for the synthesis of anilines uses the primary amination of C-H bonds in electron-rich arenes. However, there are limitations to this strategy: the amination of electron-deficient arenes remains a challenging task and the amination of electron-rich arenes has a limited control over regioselectivity-the formation of meta-aminated products is especially difficult. Here we report a site-directed C-C bond primary amination of simple and readily available alkylarenes or benzyl alcohols for the direct and efficient preparation of anilines. This chemistry involves a novel C-C bond transformation and offers a versatile protocol for the synthesis of substituted anilines. The use of O-2 as an environmentally benign oxidant is demonstrated, and studies on model compounds suggest that this method may also be used for the depolymerization of lignin. |
URI | http://hdl.handle.net/20.500.11897/543565 |
ISSN | 1755-4330 |
DOI | 10.1038/s41557-018-0156-y |
Indexed | CCR IC SCI(E) EI |
Appears in Collections: | 天然药物与仿生药物国家重点实验室 |