双功能MoNi4电极实现水参与的氮杂环化合物转移氢化与脱氢

doi:10.1016/S1872-2067(21)63834-2

催化学报 ›› 2021, Vol. 42 ›› Issue (11): 1983-1991.DOI: 10.1016/S1872-2067(21)63834-2

双功能MoNi₄电极实现水参与的氮杂环化合物转移氢化与脱氢

李孟阳^a^,^c,†, 刘翠波^a,†, 黄义^a, 韩舒艳^a, 张兵^a^,^b^,^*()

^a天津大学理学院化学系, 分子+研究院, 天津300072
^b天津大学教育部合成生物前沿科学中心, 天津市分子光电科学重点实验室, 天津300072
^c郑州大学化学学院, 河南郑州450001

收稿日期:2021-02-26 修回日期:2021-02-26 接受日期:2021-05-04 出版日期:2021-11-18 发布日期:2021-05-18
通讯作者: 张兵
作者简介:^*电话: (022)27406140; 传真: (022)27403475; 电子信箱: bzhang@tju.edu.cn
第一联系人：^†共同第一作者.
基金资助:
国家自然科学基金(21871206);国家自然科学基金(22001192)

Water-involving transfer hydrogenation and dehydrogenation of N-heterocycles over a bifunctional MoNi₄ electrode

Mengyang Li^a^,^c,†, Cuibo Liu^a,†, Yi Huang^a, Shuyan Han^a, Bing Zhang^a^,^b^,^*()

^aDepartment of Chemistry, School of Science, Institute of Molecular Plus, Tianjin University, Tianjin 300072, China
^bFrontiers Science Center for Synthetic Biology (Ministry of Education), Tianjin Key Laboratory of Molecular Optoelectronic Sciences Tianjian University, Tianjin 300072, China
^cCollege of Chemistry, Zhengzhou University, Zhengzhou 450001, Henan, China

Received:2021-02-26 Revised:2021-02-26 Accepted:2021-05-04 Online:2021-11-18 Published:2021-05-18
Contact: Bing Zhang
About author:^*Tel: +86-22-27406140; Fax: +86-22-27403475; E-mail: bzhang@tju.edu.cn
Bing Zhang (Department of Chemistry, School of Science, Tianjin University) received his Ph.D. degree from the University of Science and Technology of China in 2007 (with Prof. Yi Xie). He carried out postdoctoral research at the University of Pennsylvania (July 2007 to July 2008, with Prof. Ritesh Agarwal) and worked as an Alexander von Humboldt fellow at the Max Planck Institute of Colloids and Interfaces (August 2008 to July 2009, with Dayang Wang). Currently, he is a Fellow of the Royal Society of Chemistry (FRSC), a senior member of the Chinese Chemical Society, and a professor at Tianjin University. He mainly focuses on the controlled chemical transformation synthesis of designed targeted nanomaterials for water splitting and water-involved transfer hydrogenation reactions. In 2020, he joined the Editorial Board of the Chinese Journal of Catalysis.First author contact:^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21871206);National Natural Science Foundation of China(22001192)

摘要/Abstract

摘要：

氮杂环的催化氢化在有机合成、药物研发、石油化工等领域有着重要应用. 尽管发展了一系列均相和非均相催化加氢体系, 但由于通常使用易燃易爆的氢气或价格昂贵且毒性较高的试剂(如: 水合肼和硼氢化钠)为氢源, 给安全生产及生态环境带来了严重的问题. 此外, 由于动力学同位素效应, 氘代药物具有重要应用. 氮杂环结构作为生物医药的构筑单元与关键中间体, 现有的策略由于没有合适的氘源难以用于氘代氮杂环化合物的合成. 因此, 急需开发一种基于非贵金属催化剂和安全易得氢(氘)源的氮杂环催化氢(氘)化策略.
水相中的电化学氢化可利用水电解原位产生的活性氢替代传统的氢气裂解实现有机氢化产物的合成, 已成为一种理想氢化策略, 被广泛应用于二氧化碳还原、硝酸根还原和生物质氢解等. 本课题组前期研究已经实现了以氘水为氘源的氘代分子的高效电化学合成(Angew. Chem. Int. Ed., 2020, 59, 18527-18531; Angew. Chem. Int. Ed., 2020, 59, 21170-21175; CCS Chem., 2021, 3, 507-515). 然而, 要开发一种电化学的杂环氢化方法, 一方面要克服氮杂环化合物对催化剂的毒化, 另一方面要在电极表面产生大量的活性氢. 因此, 开发具有较好的水离解性能的非贵金属电极材料是实现氮杂芳烃电化学氢化和氘代的关键. 基于上述要求, MoNi₄(目前用于碱性电催化水分解制氢的活性较高的非贵金属材料)成为理想的电极材料.
本文以喹喔啉(1,2,3,4-四氢喹喔啉骨架作为重要的结构单元存在于许多生物活性化合物中)作为模板底物, 设计并制备了三维自支撑的MoNi₄多孔纳米片为双功能电极, 以水和氘水为氢源和氘源, 实现了喹喔啉及其他氮杂环分子的氢化与氢化, 同时实现了四氢喹喔啉的电化学氧化脱氢. 制备了MoNi₄纳米片阵列, 利用扫描电子显微镜、透射电子显微镜、X射线衍射和X光电子能谱等手段进行表征, 评估了其在碱性电解液中用于喹喔啉电化学转移氢化的性能. 结果表明, MoNi₄电极加速了动力学缓慢的Volmer步骤, 在仅50 mV的过电势下以80%的法拉第效率实现了喹喔啉的电化学氢化. 电子顺磁共振等证实水电解生成了H*, 并与喹喔啉自由基阴离子偶联实现喹喔啉的氢化. 同时, 该电化学转移氢化方法可很好地应用于一系列喹喔啉衍生物和其他氮杂芳烃化合物. 克级合成体现了该电化学转移氢化方法的潜在应用性. 原位拉曼实验结果表明, 在MoNi₄表面形成的NiOOH是实现1,2,3,4-四氢喹喔啉氧化脱氢的重要物种. 此外, 以D₂O代替H₂O, 可以较好的收率和高达99%的氘化率实现氘代氮杂环的合成. 与传统的氮杂环氢化方法相比, 本文的电化学转移氢化策略具有绿色、温和、高效的特点, 同时拓宽了电化学氢化在合成化学中的应用.

关键词: 电催化, 转移氢化, 氘代, 水为氢源, 双功能电极

Abstract:

A room-temperature electrochemical strategy for hydrogenation (deuteration) and reverse dehydrogenation of N-heterocycles over a bifunctional MoNi₄ electrode is developed, which includes the hydrogenation of quinoxaline using H₂O as the hydrogen source with 80% Faradaic efficiency and the reverse dehydrogenation of hydrogen-rich 1,2,3,4-tetrahydroquinoxaline with up to 99% yield and selectivity. The in situ generated active hydrogen atom (H*) is plausibly involved in the hydrogenation of quinoxaline, where a consecutive hydrogen radical coupled electron transfer pathway is proposed. Notably, the MoNi₄ alloy exhibits efficient quinoxaline hydrogenation at an overpotential of only 50 mV, owing to its superior water dissociation ability to provide H* in alkaline media. In situ Raman tests indicate that the Ni^II/Ni^III redox couple can promote the dehydrogenation process, representing a promising anodic alternative to low-value oxygen evolution. Impressively, electrocatalytic deuteration is easily achieved with up to 99% deuteration ratios using D₂O. This method is capable of producing a series of functionalized hydrogenated and deuterated quinoxalines.

Key words: Electrocatalysis, Transfer hydrogenation, Deuteration, Water as the hydrogen source, Bifunctional electrode

李孟阳, 刘翠波, 黄义, 韩舒艳, 张兵. 双功能MoNi₄电极实现水参与的氮杂环化合物转移氢化与脱氢[J]. 催化学报, 2021, 42(11): 1983-1991.

Mengyang Li, Cuibo Liu, Yi Huang, Shuyan Han, Bing Zhang. Water-involving transfer hydrogenation and dehydrogenation of N-heterocycles over a bifunctional MoNi₄ electrode[J]. Chinese Journal of Catalysis, 2021, 42(11): 1983-1991.

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图/表 6

Fig. 1. (a) Reported homogeneous and heterogeneous catalytic hydrogenation of N-heteroarenes. (b) Electrocatalytic transfer hydrogenation/deuteration using H2O or D2O and reverse dehydrogenation of N-heterocycles over a bifunctional MoNi4 electrode.

Fig. 2. (a) SEM image of MoNi4 nanosheet arrays. TEM (b,c) and HRTEM (d) images of MoNi4 nanosheets; (e-g) Elemental mapping of MoNi4 nanosheets; (h) XRD patterns of powder scratched from the MoNi4 electrode; (i,j) Ni 2p and Mo 3d XPS profiles for MoNi4 nanosheets.

Fig. 3. (a) LSV curves of MoNi4 cathode at a scan rate of 1 mV s-1 in 10 mL of 1.0 M KOH with and without 10 mM of 1a. (b) Potential-dependent FEs and selectivity of 2a. Conditions: 1a (0.1 mmol), MoNi4 electrode (working area: 1.0 cm2), 1.0 M KOH (7.0 mL), 38.5 C charge transferred, room temperature. (c) Comparison with other electrodes. Conditions: 1a (0.1 mmol), electrode (working area: 1.0 cm2), 1.0 M KOH (7.0 mL), -0.5 V vs. RHE, 38.5 C charge transferred. (d) Time-dependent evolution of 1a, fully and half-hydrogenated products 2a and DHQ. 48 C transferred for the full conversion of 0.1 mmol of 1a. (e) J-t curve of MoNi4 at -0.05 V vs. RHE with intermittent addition of 0.1 mmol of 1a. (f) Cycle-dependent yields and FEs of 2a. 48 C transferred for each cycle. Conv. = Conversion. Sel. = Selectivity.

Fig. 4. (a) LSV curves of glassy carbon cathode at a scan rate of 5 mV s-1 in 10 mL of 1.0 M KOH with and without 10 mM of 1a; (b) Spin trapping of hydrogen radical; (c) Transformations of 1a with and without the addition of t-BuOH; (d) HPLC chromatograms acquired at various electrolysis times; (e) Proposed mechanism.

Fig. 5. Substrate scope of electrocatalytic transfer hydrogenation/deuteration of N-heteroarenes with H2O or D2O over MoNi4 cathode. a Reaction conditions: 1 (0.3 mmol), MoNi4 electrode (working area: 1.0 cm2), 1.0 M KOH (Diox/H2O, 1:6 v/v, 7 mL), room temperature, constant current = 25 mA, 6 h. b 10 h. c 1.0 M K2CO3 (Diox/D2O, 1:6 v/v, 7 mL). Conversion yields of 1 are reported. Numbers in parentheses are the selectivity of 2.

Fig. 6. (a) LSV curves of MoNi4 anode at a scan rate of 5 mV s-1 in 10 mL of 1.0 M KOH with and without 10 mM of 2a; (b) Potential-dependent in situ Raman tests; (c) Time-dependent in situ Raman tests at 1.45 V vs. RHE in 1.0 M KOH solution in the presence of 10 mM of 2a; (d) Proposed process for dehydrogenation of 2a over MoNi4 anode; (e) LSV curves and comparison of potential for achieving benchmark current densities (10 and 20 mA cm-2) over MoNi4 || MoNi4 electrolyzer in 1.0 M KOH with and without 10 mM of 2a.

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双功能MoNi₄电极实现水参与的氮杂环化合物转移氢化与脱氢

Water-involving transfer hydrogenation and dehydrogenation of N-heterocycles over a bifunctional MoNi₄ electrode

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[1]	唐小龙, 李锋, 李方, 江燕斌, 余长林. 单原子催化剂在光催化和电催化合成过氧化氢中的研究进展[J]. 催化学报, 2023, 52(9): 79-98.
[2]	张季, 俞爱民, 孙成华. 非金属掺杂石墨烯异核双原子催化剂氮还原特性研究[J]. 催化学报, 2023, 52(9): 263-270.
[3]	胡金念, 田玲婵, 王海燕, 孟洋, 梁锦霞, 朱纯, 李隽. MXene负载3d金属单原子高效氮还原电催化剂的理论筛选[J]. 催化学报, 2023, 52(9): 252-262.
[4]	洪岩, 王琦, 阚子旺, 张禹烁, 郭晶, 李思琦, 刘松, 李斌. 电化学氮还原氨反应催化剂的最新研究进展[J]. 催化学报, 2023, 52(9): 50-78.
[5]	刘勇, 赵晓丽, 隆昶, 王晓艳, 邓邦为, 李康璐, 孙艳娟, 董帆. 原位构筑动态Cu/Ce(OH)_x界面用于高活性、高选择性和高稳定性硝酸盐还原合成氨[J]. 催化学报, 2023, 52(9): 196-206.
[6]	高晖, 张恭, 程东方, 王永涛, 赵静, 李晓芝, 杜晓伟, 赵志坚, 王拓, 张鹏, 巩金龙. 构建Cu台阶位促进电催化CO₂还原制醇类化学品的研究[J]. 催化学报, 2023, 52(9): 187-195.
[7]	邹心仪, 顾均. 酸性条件下二氧化碳高效电还原策略[J]. 催化学报, 2023, 52(9): 14-31.
[8]	周波, 石建巧, 姜一民, 肖磊, 逯宇轩, 董帆, 陈晨, 王特华, 王双印, 邹雨芹. 强化脱氢动力学实现超低电池电压和大电流密度下抗坏血酸电氧化[J]. 催化学报, 2023, 50(7): 372-380.
[9]	王元男, 王立娜, 张可新, 徐靖尧, 武倩楠, 谢周兵, 安伟, 梁宵, 邹晓新. 钙钛矿氧化物在水裂解反应中的电催化研究[J]. 催化学报, 2023, 50(7): 109-125.
[10]	周纳, 王家志, 张宁, 王志, 王恒国, 黄岗, 鲍迪, 钟海霞, 张新波. 富含缺陷的Cu@CuTCNQ复合材料增强电催化硝酸盐还原成氨[J]. 催化学报, 2023, 50(7): 324-333.
[11]	李轩, 蒋兴星, 孔艳, 孙建桔, 胡琪, 柴晓燕, 杨恒攀, 何传新. GaN/In₂O₃的界面工程用于高效电催化CO₂还原制备甲酸[J]. 催化学报, 2023, 50(7): 314-323.
[12]	Sang Eon Jun, Sungkyun Choi, Jaehyun Kim, Ki Chang Kwon, Sun Hwa Park, Ho Won Jang. 用于电化学能量转换反应的非贵金属单原子催化剂[J]. 催化学报, 2023, 50(7): 195-214.
[13]	牛青, 米林华, 陈玮, 李秋军, 钟升红, 于岩, 李留义. 基于共价有机框架的单位点光(电)催化材料的研究进展[J]. 催化学报, 2023, 50(7): 45-82.
[14]	欧阳玲, 梁杰, 罗永嵩, 郑冬冬, 孙圣钧, 刘倩, Mohamed S. Hamdy, 孙旭平, 应斌武. 电催化合成氨的研究进展[J]. 催化学报, 2023, 50(7): 6-44.
[15]	李静静, 张锋伟, 詹新雨, 郭河芳, 张涵, 昝文艳, 孙振宇, 张献明. 酞菁镍分子结构的精确设计: 优化电子和空间效应用于CO₂电还原[J]. 催化学报, 2023, 48(5): 117-126.