银催化羧化偶联反应及钌催化交叉复分解反应串联合成官能团炔酸酯

doi:10.1016/S1872-2067(12)60527-0

催化学报 ›› 2013, Vol. 34 ›› Issue (6): 1179-1186.DOI: 10.1016/S1872-2067(12)60527-0

银催化羧化偶联反应及钌催化交叉复分解反应串联合成官能团炔酸酯

张琳琳, 张文珍, 石凌龙, 任祥, 吕小兵

大连理工大学精细化工国家重点实验室, 辽宁大连116024

收稿日期:2012-12-07 修回日期:2013-01-07 出版日期:2013-06-07 发布日期:2013-06-09
通讯作者: 张文珍,吕小兵
基金资助:
国家自然科学基金(20802007, 21111120073); 中央高校基本科研业务费专项资金(DUT12LK47); 辽宁省教育厅科研项目(L2012024).

Sequential Ag-catalyzed carboxylative coupling/Ru-catalyzed cross-metathesis reactions for the synthesis of functionalized 2-alkynoates

ZHANG Linlin, ZHANG Wenzhen, SHI Linglong, REN Xiang, Lü Xiaobing

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, Liaoning China

Received:2012-12-07 Revised:2013-01-07 Online:2013-06-07 Published:2013-06-09
Supported by:
This work was supported by the National Natural Science Foundation of China (20802007, 21111120073), the Fundamental Research Funds for the Central Universities (DUT12LK47), and the Scientific Research Fund of Liaoning Provincial Education Department (L2012024).

摘要/Abstract

摘要：

通过将Ag催化的羧化偶联反应与Ru催化的交叉复分解反应串联, 用端炔、二氧化碳、端烯基取代的溴代物和甲基丙烯酸甲酯高效高产率地合成了一系列官能团化的炔酸酯.

关键词: 二氧化碳, 羧化偶联反应, 银催化剂, 交叉复分解反应, Grubbs-Hoveyda催化剂, 均相催化

Abstract:

Sequential reactions can provide efficient access to a variety of important organic compounds that would be otherwise difficult to obtain using conventional methods and readily available starting materials. Based on the importance of 2-alkynoates in organic synthesis, the current research aimed to develop a method for the convenient synthesis of functionalized 2-alkynoates from terminal alkynes, CO₂, terminal alkene-derived bromides, and methyl acrylate using a combination of the carboxylative coupling and cross-metathesis reactions. The initial ligand-free silver-catalyzed carboxylative coupling reactions of a variety of different aryl-substituted terminal alkynes and CO₂ with 5-bromopentene and 6-bromohexene provided a series of 4-pentenyl 2-alkynoates and 5-hexenyl 2-alkynoates, respectively, in good yield. These resulting 2-alkynoates were further transformed into methyl (E)-6-acetylenecarboxy-2-hexenoates and (E)-7-acetylenecarboxy-2-heptenoates in moderate to good yields by their cross-metathesis reactions with methyl acrylate in the presence of the Grubbs-Hoveyda catalyst. All of the new products characterized spectroscopically.

Key words: Carbon dioxide, Carboxylative coupling, Silver catalyst, Cross-metathesis, Grubbs-Hoveyda catalyst, Homogeneous catalysis

张琳琳, 张文珍, 石凌龙, 任祥, 吕小兵. 银催化羧化偶联反应及钌催化交叉复分解反应串联合成官能团炔酸酯[J]. 催化学报, 2013, 34(6): 1179-1186.

ZHANG Linlin, ZHANG Wenzhen, SHI Linglong, REN Xiang, Lü Xiaobing. Sequential Ag-catalyzed carboxylative coupling/Ru-catalyzed cross-metathesis reactions for the synthesis of functionalized 2-alkynoates[J]. Chinese Journal of Catalysis, 2013, 34(6): 1179-1186.

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银催化羧化偶联反应及钌催化交叉复分解反应串联合成官能团炔酸酯

Sequential Ag-catalyzed carboxylative coupling/Ru-catalyzed cross-metathesis reactions for the synthesis of functionalized 2-alkynoates

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