Synthesis of unsymmetric 1,3-diynes from bromoallenes using the catalysis of CuI and amino acid
文献类型：期刊论文
| 作者 | Jiang, Wenfang2; Shao, Guanghua2; Liu, Ying1; Du, Xin2 |
| 刊名 | CHEMICAL PAPERS
 |
| 出版日期 | 2019-10-25 |
| 页码 | 7 |
| 关键词 | Bromoallenes Unsymmetric 1,3-Diynes CuI/amino acid |
| ISSN号 | 2585-7290 |
| DOI | 10.1007/s11696-019-00962-z |
| 英文摘要 | Unsymmetric 1,3-diynes were synthesized by using bromoallenes as the starter substrates over the catalysts of CuI and amino acid. l-Proline was chosen as the amino acid as a suitable ligand of CuI. Inorganic bases, especially Cs2CO3, obviously facilitated the reaction. After screening the reaction solvents, such as CH2Cl2, DMF, Et2O, C6H5CH3, THF, CH3CN, DMSO and CH3C(O)CH3, DMSO was chosen as the best reaction solvent, and within the solvent, the yield of unsymmetric 1,3-diynes could achieve the good value of 72%. Under optimum conditions of CuI/l-proline, Cs2CO3 and DMSO, bromoallenes with methyl-, bromo- or chloro-groups in the para-position of aromatic rings gave more than 61% yields of unsymmetric 1,3-diynes. When bromoallenes had the ortho- or meta-bromine groups, the reaction failed and there were no products. The mechanism of formation of unsymmetric 1,3-diyne was also proposed as both processes of isomerization and subsequent elimination, which were catalyzed by the coupling of CuI with l-proline. Graphic abstract Scheme 1 Graphic abstract for the synthesis of unsymmetric 1,3-diynes [GRAPHICS] . |
| WOS关键词 | TERMINAL ALKYNES ; SELECTIVE SYNTHESIS ; CONJUGATED DIYNES ; COUPLING REACTION ; OXIDANT |
| 资助项目 | National Natural Science Foundation of China[21576264] ; National Natural Science Foundation of China[21776285] ; National Natural Science Foundation of China[21571027] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000492341800001 |
| 出版者 | SPRINGER INTERNATIONAL PUBLISHING AG |
| 资助机构 | National Natural Science Foundation of China |
| 源URL | [http://ir.ipe.ac.cn/handle/122111/39070]  |
| 专题 | 中国科学院过程工程研究所 |
| 通讯作者 | Liu, Ying; Du, Xin |
| 作者单位 | 1.Chinese Acad Sci, CAS Key Lab Green Proc & Engn, State Key Lab Multiphase Complex Syst, Inst Proc Engn, Beijing 100190, Peoples R China 2.Dalian Univ Technol, Coll Chem, Dalian 116012, Peoples R China |
| 推荐引用方式 GB/T 7714 | Jiang, Wenfang,Shao, Guanghua,Liu, Ying,et al. Synthesis of unsymmetric 1,3-diynes from bromoallenes using the catalysis of CuI and amino acid[J]. CHEMICAL PAPERS,2019:7. |
| APA | Jiang, Wenfang,Shao, Guanghua,Liu, Ying,&Du, Xin.(2019).Synthesis of unsymmetric 1,3-diynes from bromoallenes using the catalysis of CuI and amino acid.CHEMICAL PAPERS,7. |
| MLA | Jiang, Wenfang,et al."Synthesis of unsymmetric 1,3-diynes from bromoallenes using the catalysis of CuI and amino acid".CHEMICAL PAPERS (2019):7. |
入库方式： OAI收割
来源：过程工程研究所
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