| 余嫒嫒,徐柯,魏文廷,谢银君.三氟甲磺酸铜(Ⅱ)催化炔烃选择性转移氢化合成顺式烯烃[J].分子催化,2023,37(4):356-366 |
| 三氟甲磺酸铜(Ⅱ)催化炔烃选择性转移氢化合成顺式烯烃 |
| Copper(II) Triflate-Catalyzed Selective Transfer Hydrogenation of Alkynes for Synthesizing Cis-Alkenes |
| 投稿时间：2023-03-26 修订日期：2023-04-25 |
| DOI：10.16084/j.issn1001-3555.2023.04.005 |
| 中文关键词: 铜催化 炔烃 异丙醇 转移氢化 立体选择性 |
| 英文关键词:copper catalysis alkyne isopropanol transfer hydrogenation stereoselective |
| 基金项目:宁波市3315计划创新团队(2020A-32-C);宁波市2025重点研发计划(2022Z156);宁波市自然科学基金(2022J287) |
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| 中文摘要: |
| 顺式烯烃是许多生物活性分子的基本结构单元, 在材料科学、 药物化学和农药等领域都有着广泛的应用. 我们以异丙醇为氢源, 研究了4,5-双二苯基膦-9,9-二甲基氧杂蒽配合三氟甲磺酸铜催化的炔烃选择性转移氢化反应, 实现了高选择性顺式烯烃(Z/E >99/1)的合成. 该反应体系不需要使用高压设备, 操作简便、 安全, 对氟、 氯和溴等卤素取代的炔烃表现出良好的底物兼容性. 最后, 进行了对比实验, 并提出了可能的反应机理. |
| 英文摘要: |
| Cis-alkenes are essential structural units in many bioactive molecules and have a wide range of applications in the field of materials science, medicinal chemistry and pesticides. Herein, a copper-catalyzed selective transfer semi-hydrogenation of alkynes to cis-alkene (up to Z/E > 99/1) was developed, in which using iPrOH as a hydrogen source and Cu(OTf)2/Xantphos as a catalyst. This reaction system does not require high-pressure equipment, which is simple and safe to operate and shows good compatibility with halogen-substituted alkynes such as fluorine, chlorine and bromine. Finally, the possible reaction mechanism was proposed on the basis of control experiments. |
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