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

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

Abstract

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

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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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(12)60527-0

https://www.cjcatal.com/EN/Y2013/V34/I6/1179

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