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多相催化CO2参与的炔烃C−H键羧基化反应研究进展

吴洁文 付慧宇 陈霄 梁长海

吴洁文, 付慧宇, 陈霄, 梁长海. 多相催化CO2参与的炔烃C−H键羧基化反应研究进展[J]. 燃料化学学报. doi: 10.19906/j.cnki.JFCT.2023002
引用本文: 吴洁文, 付慧宇, 陈霄, 梁长海. 多相催化CO2参与的炔烃C−H键羧基化反应研究进展[J]. 燃料化学学报. doi: 10.19906/j.cnki.JFCT.2023002
WU Jie-wen, FU Hui-yu, CHEN Xiao, LIANG Chang-hai. Advances in Heterogeneous Catalytic C−H Bond Carbonylation of Alkynes with CO2[J]. Journal of Fuel Chemistry and Technology. doi: 10.19906/j.cnki.JFCT.2023002
Citation: WU Jie-wen, FU Hui-yu, CHEN Xiao, LIANG Chang-hai. Advances in Heterogeneous Catalytic C−H Bond Carbonylation of Alkynes with CO2[J]. Journal of Fuel Chemistry and Technology. doi: 10.19906/j.cnki.JFCT.2023002

多相催化CO2参与的炔烃C−H键羧基化反应研究进展

doi: 10.19906/j.cnki.JFCT.2023002
基金项目: 国家自然科学基金(22272014),辽宁省“兴辽英才计划”(XLYC1908033),大连市重点领域创新团队支持计划项目 (2019RT10)和中央高校基本科研业务费(DUT21TD103和DUT21LK02)资助
详细信息
    通讯作者:

    Tel: + 86-0411-84986353, Fax: + 86-0411-84986353, E-mail: xiaochen@dlut.edu.cn

    changhai@dlut.edu.cn

  • 中图分类号: TQ519

Advances in Heterogeneous Catalytic C−H Bond Carbonylation of Alkynes with CO2

Funds: The project was supported by the the National Natural Science Foundation of China (22272014), Liaoning Revitalization Talent Program (XLYC1908033), Dalian Innovation Team Support Plan in Key Areas (2019RT10) and the Fundamental Research Funds for the Central Universities (DUT21TD103 and DUT21LK02)
  • 摘要: 炔烃C−H键与CO2羧基化生成丙炔酸类化合物符合原子经济理念,在有机、医药中间体合成领域具有重要研究意义。在“碳达峰、碳中和”的背景下,该反应也是一种实现CO2高值化利用的有效途径。目前,该反应体系主要通过均相催化进行,但由于多相催化体系易于分离、回收等优点,多相催化炔烃C−H键与CO2羧基化也逐步引起了关注。基于C−H键和CO2的活化机制,目前围绕铸币金属催化剂开展了相关研究,通过铸币金属与载体协同作用,促进C−C键的耦合,实现丙炔酸类化合物的合成。本文系统综述了炔烃C−H键与CO2羧基化的多相催化体系,对体系活化、羧基化反应机理、催化剂的结构特性进行了分析和总结,为后期开发高效羧基化多相催化剂及相关工艺提供了研究思路。
  • 图  1  炔酸(酯)类化合物的应用[15]

    Figure  1  Application of alkynic acid(ester)compounds (Reprinted with permission from ref. 15. Copyright 2015 American Chemical Society)

    图  2  xAg@ZIF-8 CTACO2 反应机理[39]

    Figure  2  CTACO2 reaction mechanism on xAg@ZIF-8 (Reprinted with permission from ref. 39. Copyright 2019 American Chemical Society)

    图  3  (a)Ag/KAPs-P,(b)Ag/KAPs-Py和(c)Ag*/KAPs-Py的合成路径[43]

    Figure  3  Synthetic Route of (a) Ag/KAPs-P, (b) Ag/KAPs-Py, and (c) Ag*/KAPs-Py aMagenta balls represent PPh3 functional groups; green balls represent Ag NPs.Solid line represents boundary of material particles.Dashed lines represent inner network of material particles. (Reprinted with permission from ref. 43. Copyright 2017 American Chemical Society)

    图  4  一锅法合成NOMP的反应途径,并经过简单“浸渍-还原”法制备Ag@NOMP[45]

    Figure  4  Illustration of the one-pot synthesis route of amine-incorporated OMP (NOMP), followed by a simple impregnation−reduction to give Ag@NOMP. (Reprinted with permission from ref. 45. Copyright 2019 American Chemical Society)

    图  5  (a)不同催化剂下苯乙炔(EB)与CO2羧化反应生成苯丙炔酸(PA)的产率(b)Ag基催化剂中Ag粒子粒径的尺寸与TON之间关系[45]

    Figure  5  (a) Comparisons of carboxylation of EB with CO2 to PA over various Ag-containing catalysts. (b) Plot for the correlation between the TON of PA produced on Ag catalysts and their particle sizes. Reaction conditions: EB (2.0 mmol), catalyst 0.1 mol%, Cs2CO3 (3 mmol), CO2 (1.0 atm), 50 ℃, DMSO (15 mL), 12 h (Reprinted with permission from ref. 45. Copyright 2019 American Chemical Society)

    图  6  核壳结构的UiO-66@UiO-67-BPY-Ag合成过程[36]

    Figure  6  synthesis of core-shell UiO-66@UiO-67-BPY-Ag (Reprinted with permission from ref. 36. Copyright 2019 American Chemical Society)

    图  7  0.2Ag@SiO2催化炔烃C-H键与CO2羧基化反应的底物拓展[46]

    Figure  7  Substrate scope of 0.2Ag@SiO2 [46] Reaction conditions: terminal alkynes (4.0 mmol), catalyst (100 mg), CO2 (1.0 atm), 70 ℃, 20 h, DMF (5 mL), and Cs2CO3 7.2 mmol (Reprinted from ref. 46, Copyright (2020) with permission from Elsevier)

    图  8  CO2插入Cu–CN-8.0和CN表面上脱质子化的苯乙炔中间体的反应路径(插图:Cu–CN-8.0的优化结构)[61]

    Figure  8  Reaction profile for CO2 inserting into the deprotonated phenylacetylene intermediate on Cu–CN-8.0 and CN surfaces (inset: the optimized structure of Cu–CN-8.0) (Reprinted with permission from ref. 61. Copyright 2020 American Chemical Society)

    图  9  Cu(IN)-MOF催化端炔与CO2羧化反应的机理[65]

    Figure  9  Proposed reaction mechanism based on the Cu(IN)-MOF catalyzed carboxylation of terminal alkynes with CO2 (Reprinted from ref. 65, Copyright (2020) with permission from Elsevier)

    图  10  TPBpy结构示意图[68]

    Figure  10  Schematic representation of TpBpy (Reprinted from ref. 68, Copyright (2021) with permission from Elsevier)

    图  11  (a) TpBpy-Cu-14催化剂的循环测试性能图;(b) 未使用的、使用过的和再生的催化剂的Cu 2p XPS谱图[68]

    Figure  11  (a) Recycling tests of the TpBpy-Cu-14,reaction condition: CO2(1 atm),1-Ethynylbenzene (1 mmol), catalyst (10 mg), Cs2CO3 (1.5 mmol), 6 h, 60 ℃. (b) Cu 2p XPS spectra of the fresh, used and regenerated catalysts (Reprinted from ref. 68, Copyright (2021) with permission from Elsevier)

    图  12  ZIF-8@Au25@ZIF-67[tkn] 和 ZIF-8@Au25@ZIF-8[tkn]的合成路径[tkn = 壳层厚度][70]

    Figure  12  Synthetic Route for the Sandwich Structures of ZIF-8@Au25@ZIF-67[tkn] and ZIF-8@Au25@ZIF-8[tkn] [tkn = Thickness of Shell] (Reprinted with permission from ref. 70. Copyright 2020 American Chemical Society)

    图  13  (A)不同催化剂催化苯乙炔羧化的反应活性 ;(B)三种不同催化剂的柱状图;(C)具有不同壳层厚度的ZIF-8@Au25@ZIF-67催化性能折线图;(D)不同催化剂的TPD-CO2[70]

    Figure  13  (A) Catalytic activity of various catalysts for the carboxylation of phenylacetylene. Reaction conditions: catalyst (1.12 × 10–4 mmol of Au25), alkyne (0.5 mmol), Cs2CO3 (0.24 mmol), CO2 (1.0 bar), 50 ℃, 12 h. (B) Column diagram of three different catalysts. (C) Broken line diagram of catalytic performance of ZIF-8@Au25@ZIF-67 with various shell thicknesses. (D) TPD-CO2 by various catalysts (Reprinted with permission from ref. 70. Copyright 2020 American Chemical Society)

    表  1  端炔与CO2直接羧化反应的Ag基催化体系

    Table  1  Heterogeneous catalytic system for direct carboxylation of terminal alkynes with carbon dioxide

    entrycatalystAg loadingReaction conditionsYield (%)TOF (h−1)Ref.
    T(℃)P(atm)t(h)solventbase
    10.5Ag@ZIF-89.63wt%40120DMFCs2CO397[39]
    2Ag@MIL-1014.16wt%50112DMFCs2CO396.5[40]
    3Ag@MIL-1003.39wt%50115DMFCs2CO394.6[41]
    4Ag@UIO-667.12wt%50115DMFCs2CO397.6[41]
    5AgNPs/Co-MOF4.40wt%80114DMFCs2CO398[28]
    6Ag@FeNT6.9wt%60515DMSOCs2CO389[42]
    7Ag/KAPs-P0.1wt%6016DMSOCs2CO374[43]
    8AgNPs/melamine-based POPs2.5wt%50115DMFCs2CO3922.23[44]
    9Ag@NOMP1.5wt%50112DMSOCs2CO396[45]
    10Ag@PHNCT0.73mol%50120DMSOCs2CO3985.48[46]
    11UiO-66@UiO-67-BPY-Ag4.38wt%50124DMFCs2CO396[36]
    120.2Ag@SiO23.34wt%70120DMFCs2CO392.55.94[47]
    13Ag/tert-GO(0.5)11.2wt%40124DMFCs2CO384.12.7[48]
    14Ag/graphene18.3wt%40124DMFCs2CO354.31.74[48]
    15Ag/graphite oxide16.9wt%40124DMFCs2CO331.70.42[48]
    16Ag/tert-GO-L15.4wt%40124DMFCs2CO343.30.63[48]
    17NPOP-1-60112DMSOCs2CO355.4[49]
    18Ag@NPOP-10.93wt%60112DMSOCs2CO394.01125.1[49]
    19CTF-DCE-Ag0.4mol%50120DMFCs2CO390.2[50]
    20Ag0CTFN3.69wt%60124DMSOCs2CO397[51]
    21Ag/PCNF-7007.2wt%25118DMSOCs2CO398[52]
    22Ag@p-CTF-2502.26wt%70116DMSOCs2CO395[53]
    23Ag@TpBpy1.9wt%6016DMSOCs2CO393[35]
    24Ag/Schiff-SiO21.20wt%60124DMSOCs2CO397[54]
    25Ag/Schiff-SiO21.20wt%60124DMFCs2CO350[54]
    下载: 导出CSV

    表  2  端炔与CO2直接羧化反应的Cu基与其它多相催化体系

    Table  2  Heterogeneous catalytic system for direct carboxylation of terminal alkynes with carbon dioxide

    entrycatalystReaction conditionsYield (%)Ref.
    T(℃)P(atm)t(h)solventbase
    1Cu-CN-880110DMFCs2CO397[61]
    2Cu(IN)-MOFs8014DMFCs2CO380[65]
    3醋酸铜8014DMFCs2CO345[65]
    4异烟酸8014DMFCs2CO30[65]
    5Cu-MOF100316DMFCs2CO388[60]
    6$ {\left[Cu{\left(Fbtx\right)}_{2}{\left({NO}_{3}\right)}_{2}\right]}_{n} $100316DMFCs2CO385[66]
    7CZU-7100316DMFCs2CO387[67]
    8TpBpy60124DMSOCs2CO379[68]
    9TpBpy-Cu-1460124DMSOCs2CO395[68]
    10Au@Ag24501012DMFCs2CO392[69]
    11ZIF-8@Au25 @ZIF-67[12]50112DMSOCs2CO399[70]
    下载: 导出CSV

    表  3  端炔与CO2的在卤代烷(RX)作用下的羧化反应

    Table  3  Carboxylation of terminal alkyne with carbon dioxide in the presence of haloalkanes


    Entry

    Catalyst
    Reaction conditionsYield
    (%)
    Ref
    T(℃)P(atm)t(h)solventbaseRX
    1Ag(3.12%)/M-CeO2(120)60524DMFCs2CO3Cinnamyl chloride91[27]
    2Ag@16016DMFCs2CO3nBuI91[76]
    3Cu nps/Al2O360216DMFCs2CO3BuBr92[63]
    4CuCl2@Poly-GLY(1-vim)3(OMs)3404012DMacCs2CO3n-BuI96[64]
    5CuBr@C8012ECCs2CO3nBuI78[15]
    下载: 导出CSV

    表  4  水在无金属催化时对于反应的影响

    Table  4  Effect of water on the catalyzed and catalyst-free reaction

    EntryNotesT(℃)Time(h)Yield(%)
    1anhydrous804>99
    20.1 equiv H2O80480
    30.2 equiv H2O80443
    41 equiv H2O804<1
    Reaction conditions: phenylacetylene (0.28 mmol), CO2(1 atm), DMSO (1 mL). Product trapped with butyl iodide (1.1 equiv.). Yields determined by GC using n-decane as internal standard
    下载: 导出CSV
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  • 收稿日期:  2022-11-20
  • 录用日期:  2022-12-24
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