| 三氟甲磺酸铜(Ⅱ)催化炔烃选择性转移氢化合成顺式烯烃 |
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| 引用本文： | 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. |
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| 作者姓名： | 余嫒嫒 徐柯 魏文廷 谢银君 |
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| 作者单位： | 宁波大学 材料科学与化学工程学院, 浙江 宁波 315211;中国科学院宁波材料技术与工程研究所浙江省先进燃料电池与电解池技术重点实验室, 浙江 宁波315201,宁波大学 材料科学与化学工程学院, 浙江 宁波 315211;中国科学院宁波材料技术与工程研究所浙江省先进燃料电池与电解池技术重点实验室, 浙江 宁波315201,宁波大学 材料科学与化学工程学院, 浙江 宁波 315211,中国科学院宁波材料技术与工程研究所浙江省先进燃料电池与电解池技术重点实验室, 浙江 宁波315201 |
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| 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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| 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.
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| 关 键 词： | 铜催化 炔烃 异丙醇 转移氢化 立体选择性 |
| 收稿时间： | 2023/3/26 0:00:00 |
| 修稿时间： | 2023/4/25 0:00:00 |
Copper(II) triflate-catalyzed selective transfer hydrogenation of alkynes for synthesizing cis-alkenes |
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| Yu Aiai,Xu Ke,WEI Wenting and XIE Yinjun.Copper(II) triflate-catalyzed selective transfer hydrogenation of alkynes for synthesizing cis-alkenes[J].Journal of Molecular Catalysis (China),2023,37(4):356-366. |
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| Authors: | Yu Aiai Xu Ke WEI Wenting and XIE Yinjun |
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| Institution: | School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, China;Key Laboratory of Advanced Fuel Cells and Electrolyzers Technology of Zhejiang Province, Ningbo Institute of Materials Technology and Engineering of the Chinese Academy of Sciences (CAS), Ningbo 315201, China,School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, China;Key Laboratory of Advanced Fuel Cells and Electrolyzers Technology of Zhejiang Province, Ningbo Institute of Materials Technology and Engineering of the Chinese Academy of Sciences (CAS), Ningbo 315201, China,School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, China and Key Laboratory of Advanced Fuel Cells and Electrolyzers Technology of Zhejiang Province, Ningbo Institute of Materials Technology and Engineering of the Chinese Academy of Sciences (CAS), Ningbo 315201, China |
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| Abstract: | 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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| Keywords: | copper catalysis alkyne isopropanol transfer hydrogenation stereoselective |
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