镍催化的卤代糖苷和卤代芳烃通过还原偶联制备芳香碳糖苷类化合物的简易方法  

Facile Preparation of Aryl C-Glycosides by Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Aryl Halides

作　　者：孙雨人 刘建东 林泉 姚建[1] 童玮琦[2] 钱群[2] Yuren Sun;Jiandong Liu;Quan Lin;Ken Yao;Weiqi Tong;Qun Qian(School of Materials Science and Engineering,Center for Supramolecular Chemistry and Catalysis,Shanghai 200444;College of Sciences,Shanghai University,Shanghai 200444)

机构地区：[1]上海大学材料科学与工程学院上海大学超分子化学与催化研究中心,上海200444 [2]上海大学理学院,上海200444

出　　处：《有机化学》2021年第4期1551-1562,共12页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(21871173)资助项目。

摘　　要：报道了在温和条件下通过镍和联吡啶催化的还原偶联反应,由C(1)-卤代糖苷和缺电子的芳基溴化物制备芳香糖苷类化合物的方法.运用该种方法可以由中等或高的α-选择性得到芳香碳糖苷类产物.包括富电子的芳香碘化物在内的多种卤代芳烃底物适用于该反应,产率在40%~95%之间.该方法可以放大到克级规模,并在此条件下将镍催化剂的用量减少到2 mol%.The preparation of C-aryl glycosides via mild Ni/bipyridine-catalyzed reductive arylation of C(1)-glycosyl halides with electron-deficient aryl bromides was developed.Moderate to high α-selectivities were achieved for C-glycosides.A broad range of aryl halides including electron-rich aryl iodides were employed to yield C-aryl glycosides in 40%-5%yields.This method can be scaled up on a gram scale by lowering the loading of nickel catalyst to 2 mol%.

关 键 词：镍催化 还原偶联 α-选择性制备 芳香碳糖苷 克级反应 

分 类 号：O625[理学—有机化学]