Li Minghong, Shang Ming, Xu Hui, Wang Xing, Dai Hui-Xiong, Yu Jin-Quan
State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry , Shanghai 20032 , China.
Department of Medicinal Chemistry, Shanghai Institute of Materia Medica , University of Chinese Academy of Sciences, Chinese Academy of Sciences , 555 Road Zu Chong Zhi , Zhangjiang Hi-Tech Park, Shanghai 201203 , China.
Org Lett. 2019 Jan 18;21(2):540-544. doi: 10.1021/acs.orglett.8b03871. Epub 2019 Jan 7.
One formidable challenge in sp C-H activation is how to achieve high para selectivity on electron-deficient arenes because such site selectivity is disfavored by the electronic bias induced by the electron-withdrawing groups. The first highly selective para-C-H acetoxylation of various benzoic acids using a nitrile-based template was realized. Removal of the template leads to para-hydroxylated benzoic acids, which are versatile intermediates for a wide range of synthetically useful transformations.
在sp C-H活化中，一个巨大的挑战是如何在缺电子芳烃上实现高对位选择性，因为这种位点选择性受到吸电子基团诱导的电子偏置的不利影响。利用腈基模板实现了各种苯甲酸的首例高选择性对位C-H乙酰氧基化反应。去除模板后得到对羟基苯甲酸，它是多种合成有用转化反应的通用中间体。
