钯催化咖啡因C—H键直接烷氧基羰基化反应生成8-酯基咖啡因衍生物  

Palladium-Catalyzed C—H Alkoxycarbonylation of Caffeines:Synthesis of 8-Ester-substituted Caffeines

作　　者：苏吕 肖含兵 苑雨萌[1] 张晓凤[1] 林深[1] 黄秋锋[1,2] 

机构地区：[1]福建师范大学化学与化工学院,福州350007 [2]福建省高分子材料重点实验室,福州350007

出　　处：《有机化学》2017年第3期630-635,共6页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.2110322;6152010615);福建省教育厅K类基金(No.JK2014010)资助项目~~

摘　　要：咖啡因羰基衍生物在药物活性及生物荧光方面表现优异性能,其简便合成方法备受关注.从咖啡因C—H键直接出发,研究了过渡金属钯配合物催化咖啡因C—H键与醇的氧化羰基化反应.以Pd Cl_2(PPh_3)_2为催化剂,以醋酸铜为氧化剂的反应体系下,不同咖啡因衍生物与不同醇均能进行氧化羰基化反应,得到了一系列8-酯基咖啡因衍生物.反应所用CO为一个大气压,操作简便,溴、烯烃和苯环等官能团都与体系有很好的兼容性.Carbonyl-substituted caffeine derivatives have attracted much attention due to their potent pharmaceutical activity and interesting fluorescent properties. An efficient synthesis of 8-ester-substituted caffeines through palladium-catalyzed C--H alkoxycarbonylation was developed. The reaction was carried out in the presence of PdCl2（PPh3）2 and Cu（OAc）2 under 101 kPa CO atmosphere in 1,4-dioxane, providing diversified 8-ester-substituted caffeines in reasonable to good yields. The ap- proach was characterized by using atmospheric pressure of carbon monoxide and broad functional group tolerance.

关 键 词：钯 C—H键活化 羰基化 咖啡因 一氧化碳 

分 类 号：O621.251[理学—有机化学]