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

doi:10.6023/cjoc201610028

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (3): 630-635.DOI: 10.6023/cjoc201610028 Previous Articles Next Articles

ARTICLE

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

苏吕^a, 肖含兵^a, 苑雨萌^a, 张晓凤^a, 林深^a, 黄秋锋^a,b

a 福建师范大学化学与化工学院福州 350007;
b 福建省高分子材料重点实验室福州 350007

收稿日期:2016-10-17 修回日期:2016-12-08 发布日期:2016-12-12
通讯作者: 黄秋锋,E-mail:qiufenghuang@fjnu.edu.cn E-mail:qiufenghuang@fjnu.edu.cn
基金资助:
国家自然科学基金（Nos.2110322，6152010615）和福建省教育厅K类基金（No.JK2014010）资助项目.

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

Su Lü^a, Xiao Hanbing^a, Yuan Yumeng^a, Zhang Xiaofeng^a, Lin Shen^a, Huang Qiufeng^a,b

a College of Chemistry & Chemical Engineering, Fujian Normal University, Fuzhou 350007;
b Fujian Key Laboratory of Polymer Materials, Fuzhou 350007

Received:2016-10-17 Revised:2016-12-08 Published:2016-12-12
Contact: 10.6023/cjoc201610028 E-mail:qiufenghuang@fjnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 2110322, 6152010615) and the Foundation of Fujian Educational Committee (No. JK2014010).

1. Palladium-Catalyzed C-H Alkoxycarbonylation of Caffeines: Synthesis of 8-Ester-substituted Caffeines.PDF(2784KB)

Abstract

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 approach was characterized by using atmospheric pressure of carbon monoxide and broad functional group tolerance.

Key words: palladium, C-H bond acitivation, carbonylation, caffeine, carbon monoxide

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Su Lü, Xiao Hanbing, Yuan Yumeng, Zhang Xiaofeng, Lin Shen, Huang Qiufeng. Palladium-Catalyzed C-H Alkoxycarbonylation of Caffeines: Synthesis of 8-Ester-substituted Caffeines[J]. Chin. J. Org. Chem., 2017, 37(3): 630-635.

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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

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