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| Synthesis of unsymmetric 1,3-diynes from bromoallenes using the catalysis of CuI and amino acid | |
| Jiang, Wenfang1; Shao, Guanghua1; Liu, Ying2; Du, Xin1 | |
| 2019-10-25 | |
| Source Publication | CHEMICAL PAPERS
 |
| ISSN | 2585-7290 |
| Pages | 7 |
| Abstract | 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] . |
| Keyword | Bromoallenes Unsymmetric 1,3-Diynes CuI/amino acid |
| DOI | 10.1007/s11696-019-00962-z |
| Language | 英语 |
| WOS Keyword | TERMINAL ALKYNES ; SELECTIVE SYNTHESIS ; CONJUGATED DIYNES ; COUPLING REACTION ; OXIDANT |
| Funding Project | National Natural Science Foundation of China[21576264] ; National Natural Science Foundation of China[21776285] ; National Natural Science Foundation of China[21571027] |
| WOS Research Area | Chemistry |
| WOS Subject | Chemistry, Multidisciplinary |
| Funding Organization | National Natural Science Foundation of China |
| WOS ID | WOS:000492341800001 |
| Publisher | SPRINGER INTERNATIONAL PUBLISHING AG |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.ipe.ac.cn/handle/122111/39071 |
| Collection | 中国科学院过程工程研究所 |
| Corresponding Author | Liu, Ying; Du, Xin |
| Affiliation | 1.Dalian Univ Technol, Coll Chem, Dalian 116012, Peoples R China 2.Chinese Acad Sci, CAS Key Lab Green Proc & Engn, State Key Lab Multiphase Complex Syst, Inst Proc Engn, Beijing 100190, Peoples R China |
| Recommended Citation 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. |
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