| Autor: |
Ling-Long Shi, Xiaobing Lü, Xiang Ren, Lin-Lin Zhang, Wen-Zhen Zhang |
| Rok vydání: |
2013 |
| Předmět: |
|
| Zdroj: |
Chinese Journal of Catalysis. 34:1179-1186 |
| ISSN: |
1872-2067 |
| DOI: |
10.1016/s1872-2067(12)60527-0 |
| Popis: |
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. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect