电催化CO2与有机化合物耦合制备增值化学品

doi:10.3969/j.issn.1000-5641.2023.01.014

华东师范大学学报（自然科学版） ›› 2023, Vol. 2023 ›› Issue (1): 140-148.doi: 10.3969/j.issn.1000-5641.2023.01.014

• CO2资源化利用 • 上一篇

电催化CO₂与有机化合物耦合制备增值化学品

王欢^1,²(), 陆嘉星^1,^2,*()

1. 华东师范大学化学与分子工程学院上海市绿色化学与化工过程绿色化重点实验室, 上海　200062
2. 崇明生态研究院, 上海　202162

收稿日期:2022-06-27 接受日期:2022-09-09 出版日期:2023-01-25 发布日期:2023-01-07
通讯作者: 陆嘉星 E-mail:hwang@chem.ecnu.edu.cn;jxlu@chem.ecnu.edu.cn
作者简介:王　欢, 女, 教授, 博士生导师, 研究方向为电化学. E-mail: hwang@chem.ecnu.edu.cn
基金资助:
国家自然科学基金 (22072046); 华东师范大学“幸福之花”先导研究基金 (2020ST2203)

Electrocatalytic coupling of CO₂ with organic compounds to value-added chemicals

Huan WANG^1,²(), Jiaxing LU^1,^2,*()

1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai　200062, China
2. Institute of Eco-Chongming, Shanghai　202162, China

Received:2022-06-27 Accepted:2022-09-09 Online:2023-01-25 Published:2023-01-07
Contact: Jiaxing LU E-mail:hwang@chem.ecnu.edu.cn;jxlu@chem.ecnu.edu.cn

摘要/Abstract

摘要：

在温和条件下, CO₂的高效固定利用是“绿色碳科学”的重要组成部分之一. 电催化CO₂与有机化合物耦合在转化利用CO₂的同时可以制备增值化学品, 有利于可持续发展. 本文概述了目前电催化CO₂与各类有机分子耦合制备有机羧酸、碳酸酯、氨基甲酸酯等化学品的方法. 并介绍了该领域的最新研究进展和机遇: 不对称电羧化反应, 包括手性源的构建; 其他反应物的新型反应, 包括电化学开环羧化和N-甲基化反应; 非牺牲阳极的电羧化反应, 包括阳极氧化反应的构建和电解池的调整等; 成对电合成反应等.

关键词: 二氧化碳, 电羧化, 电催化, 有机电合成

Abstract:

The efficient fixation and utilization of CO₂ under mild conditions is one of the key components of green carbon science. The electrocatalytic coupling of CO₂ and organic compounds can produce value-added chemicals, which is beneficial to sustainable development. In this review, we summarize the current methods of synthesizing carboxylic acids, organic carbonates, carbamates, and other chemicals via electrocatalytic CO₂ coupling with organic compounds. We also present the latest research progress and opportunities in this field, such as asymmetric electrocarboxylation to construct chiral molecules, electrochemical ring-opening carboxylation, electrochemical N-methylation, electrocarboxylation with non-sacrificial anodes, and paired electrosynthesis.

Key words: carbon dioxide, electrocarboxylation, electrocatalysis, electroorganic synthesis

中图分类号:

O646

王欢, 陆嘉星. 电催化CO₂与有机化合物耦合制备增值化学品[J]. 华东师范大学学报（自然科学版）, 2023, 2023(1): 140-148.

Huan WANG, Jiaxing LU. Electrocatalytic coupling of CO₂ with organic compounds to value-added chemicals[J]. Journal of East China Normal University(Natural Science), 2023, 2023(1): 140-148.

图/表 8

图1

图2

图3

图4

图5

图6

图7

图8

参考文献 46

1	HE M Y, SUN Y H, HAN B X. Green carbon science: Efficient carbon resource processing, utilization, and recycling towards carbon neutrality. Angewandte Chemie-International Edition, 2022, 61 (15): e202112835.
2	LIANG H Q, BEWERIES T, FRANCKE R, et al. Molecular catalysts for the reductive homocoupling of CO₂ towards C₂₊ compounds . Angewandte Chemie-International Edition, 2022, 61 (19): e202200723.
3	XU S Z, CARTER E A. Theoretical insights into heterogeneous (photo)electrochemical CO₂ reduction . Chemical Reviews, 2019, 119, 6631- 6669.
4	LEE S, KIM D, LEE J. Electrocatalytic oroduction of C3-C4 compounds by conversion of CO₂ on a chloride-induced Bi-phasic Cu₂O-Cucatalyst . Angewandte Chemie-International Edition, 2015, 54 (49): 14701- 14705.
5	ANG N W J, OLIVEIRA J C A, ACKERMANN L. Electroreductive cobalt-catalyzed carboxylation: Cross-electrophile electrocoupling with atmospheric CO₂. Angewandte Chemie-International Edition, 2020, 59 (31): 12842- 12847.
6	LAN Y C, WANG H, WU L X, et al. Electroreduction of dibromobenzenes on silver electrode in the presence of CO₂. Journal of Electroanalytical Chemistry, 2012, 664, 33- 38.
7	MENA S, SANTIAGO S, GALLARDO I, et al. Sustainable and efficient electrosynthesis of naproxen using carbon dioxide and ionic liquids. Chemosphere, 2020, 245, 125557.
8	YANG H P, WU L X, WANG H, et al. Cathode made of compacted silver nanoparticles for electrocatalytic carboxylation of 1-phenethyl bromide with CO₂. Chinese Journal of Catalysis, 2016, 37, 994- 998.
9	YANG D T, ZHU M H, SCHIFFER Z J, et al. Direct electrochemical carboxylation of benzylic C–N bonds with carbon dioxide. ACS Catalysis, 2019, 9 (5): 4699- 4705.
10	SENBOKU H, SAKAI K, FUKUI A, et al. Efficient synthesis of mandel acetates by electrochemical carboxylation of benzal diacetates. ChemElectroChem, 2019, 6 (16): 4158- 4164.
11	ZHONG J S, YANG Z X, DING C L, et al. Desulfonylative electrocarboxylation with carbon dioxide. The Journal of Organic Chemistry, 2021, 86, 16162- 16170.
12	QUAN Y L, YU R H, ZHU J X, et al. Efficient carboxylation of styrene and carbon dioxide by single-atomic copper electrocatalyst. Journal of Colloid and Interface Science, 2021, 601, 378- 384.
13	ALKAYAL A, TABAS V, MONTANARO S, et al. Harnessing applied potential: Delective β-hydrocarboxylation of substituted olefins. Journal of the American Chemical Society, 2020, 142, 1780- 1785.
14	KIM Y, PARK G D, BALAMURUGAN M, et al. Electrochemical β-selective hydrocarboxylation of styrene using CO₂ and water . Advanced Science, 2020, 7 (3): 1900137.
15	GHOBADI K, ZARE H R, KHOSHRO H, et al. Electrosynthesis of cinnamic acid by electrocatalytic carboxylation of phenylacetylene in the presence of [NiⅡ(Me4-NO2Bzo[15]tetraeneN4)] complex: An EC′ CCC′ C mechanism. Comptes Rendus Chimie, 2018, 21, 14- 18.
16	LI C H, YUAN G Q, JIANG H F. Electrocarboxylation of alkynes with carbon dioxide in the presence of metal salt catalysts. Chinese Journal of Chemistry, 2010, 28, 1685- 1689.
17	STALCUP M A, NILLES C K, LEE H J, et al. Organic electrosynthesis in CO₂-eXpanded electrolytes: Enabling selective acetophenone carboxylation to atrolatic acid . ACS Sustainable Chemistry & Engineering, 2021, 9 (31): 10431- 10436.
18	SENBOKU H, YAMAUCHI Y, FUKUHARA T, et al. Electrochemical carboxylation of aliphatic ketones: Synthesis of beta-keto carboxylic acids. Electrochemistry, 2006, 74, 612- 614.
19	WANG H, ZHU H W, GUO R R, et al. Computational and experimental study on electrocarboxylation of benzalacetone. Asian Journal of Organic Chemistry, 2017, 6 (10): 1380- 1384.
20	QU Y, TSUNEISHI C, TATENO H, et al. Green synthesis of α-amino acids by electrochemical carboxylation of imines in a flow microreactor. Reaction Chemistry & Engineering, 2017, 2 (6): 871- 875.
21	WU L X, YANG H P, GUAN Y B, et al. Electrosynthesis of cyclic carbonates from CO₂ and epoxides on compacted silver nanoparticles electrode . International Journal of Electrochemical Science, 2017, 12 (10): 8963- 8972.
22	WANG H, WU L X, ZHAO J Q, et al. Synthesis of cyclic carbonates from CO₂ and diols via electrogenerated cyanomethyl anion . Greenhous Gases-Science and Technology, 2012, 2 (1): 59- 65.
23	LEE K M, JANG J H, BALAMURUGAN M, et al. Redox-neutral electrochemical conversion of CO₂ to dimethyl carbonate . Nature Energy, 2021, 6, 733- 741.
24	FORTE G, CHIAROTTO I, RICHTER F, et al. Towards a sustainable electrochemical activation for recycling CO₂: Synthesis of bis-O-alkylcarbamates from aliphatic and benzyl diamines . Reaction Chemistry & Engineering, 2017, 2 (5): 646- 649.
25	TASCEDDA P, DUNACH E. Electrosynthesis of cyclic carbamates from aziridines and carbon dioxide [J]. Chemical Communications, 2000(6): 449-450.
26	ORSINI M, FEROCI M, SOTGIU G, et al. Stereoselective electrochemical carboxylation: 2-phenylsuccinates from chiral cinnamic acid derivatives. Organic & Biomolecular Chemistry, 2005, 3 (7): 1202- 1208.
27	FEROCI M, INESI A, ORSINI M, et al. Electrochemical carboxylation of N-(2-bromopropionyl)-4R-phenyloxazolidin-2-one: An efficient route to unsymmetrical methylmalonic ester derivatives. Organic Letters, 2002, 4 (16): 2617- 2620.
28	CHEN B L, TU Z Y, ZHU H W, et al. CO₂ as a C1-organic building block: Enantioselective electrocarboxylation of aromatic ketones with CO₂ catalyzed by cinchona alkaloids under mild conditions . Electrochimica Acta, 2014, 116, 475- 483.
29	CHEN B L, ZHU H W, XIAO Y, et al. Asymmetric electrocarboxylation of 1-phenylethyl chloride catalyzed by electrogenerated chiral [COI(salen)]- complex. Electrochemistry Communications, 2014, 42, 55- 59.
30	JIAO K J, LI Z M, XU X T, et al. Palladium-catalyzed reductive electrocarboxylation of allyl esters with carbon dioxide. Organic Chemistry Frontiers, 2018, 5 (14): 2244- 2248.
31	YANG H P, YUE Y N, SUN Q L, et al. Entrapment of a chiral cobalt complex within silver: A novel heterogeneous catalyst for asymmetric carboxylation of benzyl bromides with CO₂. Chemical Communications, 2015, 51, 12216- 12219.
32	YANG H P, CHI D H, SUN Q L, et al. Entrapment of alkaloids within silver: From enantioselective hydrogenation to chiral recognition. Chemical Communications, 2014, 50, 8868- 8870.
33	YANG H P, FEN Q, WANG H, et al. Copper encapsulated alkaloids composite: An effective heterogeneous catalyst for electrocatalytic asymmetric hydrogenation. Electrochemistry Communications, 2016, 71, 38- 42.
34	YANG L R, ZHANG J J, ZHAO Y J, et al. La_1−xSr_xFeO₃perovskite electrocatalysts for asymmetric electrocarboxylation of acetophenone with CO₂. Electrochimica Acta, 2021, 398, 139308.
35	YANG L R, ZHAO Y J, JIANG C J, et al. Perovskite La_0.7Sr_0.3Fe_0.8B_0.2O₃ (B = Ti, Mn, Co, Ni, and Cu) as heterogeneous electrocatalysts for asymmetric electrocarboxylation of aromatic ketones . Jouranl Catalysis, 2021, 401, 224- 233.
36	ZHAO Y J, YANG L R, WANG L T, et al. Asymmetric electrocarboxylation of 4′ -methylacetophenone over PrCoO₃ perovskites . Catalysis Science & Technology, 2022, 12 (9): 2887- 2893.
37	LIAO L L, WANG Z H, CAO K G, et al. Electrochemical ring-opening dicarboxylation of strained carbon–carbon single bonds with CO₂: Facile synthesis of diacids and derivatization into polyesters . Journal of the American Chemical Society, 2022, 144, 2062- 2068.
38	SUN X F, ZHU Q G, HU J Y, et al. N,N-Dimethylation of nitrobenzenes with CO₂ and water by electrocatalysis . Chemical Science, 2017, 8 (8): 5669- 5674.
39	ROONEY C L, WU Y S, TAO Z X, et al. Electrochemical eeductive N-methylation with CO₂ enabled by a molecular catalyst . Journal of the American Chemical Society, 2021, 143, 19983- 19991.
40	SENBOKU H, NAGAKURA K, FUKUHARA T, et al. Three-component coupling reaction of benzylic halides, carbon dioxide, and N, N-dimethylformamide by using paired electrolysis: Sacrificial anode-free efficient electrochemical carboxylation of benzylic halides. Tetrahedron, 2015, 71, 3850- 3856.
41	GRINBERG V A, KOCH T A, MAZIN V M, et al. Electrocarboxylation of 1,4-dibromobut-2-ene in a CO₂-DMF liquid mixture . Russian Chemical Bulletin, 1997, 46, 1560- 1564.
42	CORBIN N, YANG D T, LAZOUSKI N, et al. Suppressing carboxylate nucleophilicity with inorganic salts enables selective electrocarboxylation without sacrificial anodes. Chemical Science, 2021, (12): 12365- 12376.
43	MEDVEDEV J J, MEDVEDEVA X V, LI F, et al. Electrochemical CO₂ fixation to α-methylbenzyl bromide in divided cells with nonsacrificial anodes and aqueous anolytes . ACS Sustainable Chemistry & Engineering, 2019, 7 (24): 19631- 19639.
44	SHETA A M, MASHALY M A, SAID S B, et al. Selective α,δ-hydrocarboxylation of conjugated dienes utilizing CO₂ and electrosynthesis . Chemical Science, 2020, 11 (34): 9109- 9114.
45	MATTHESSEN R, FRANSAER J, BINNEMANS K, et al. Paired electrosynthesis of diacid and diol precursors using dienes and CO₂ as the carbon source . ChemElectroChem, 2015, 2 (1): 73- 76.
46	MUCHEZ L, DE VOS D E, KIM M J. Sacrificial anode-free electrosynthesis of α-hydroxy acids via electrocatalytic coupling of carbon dioxide to aromatic alcohols. ACS Sustainable Chemistry & Engineering, 2019, 7 (19): 15860- 15864.

[1]	楚萌恩, 陈春俊, 吴海虹, 何鸣元, 韩布兴. 电沉积制备铜基催化剂及其对CO₂电还原的催化性能[J]. 华东师范大学学报（自然科学版）, 2023, 2023(1): 129-139.
[2]	亓西敏;杜艳芳;张贵荣;赵鹏;陆嘉星. 聚苯胺在离子液体中的电合成及其电催化性质[J]. 华东师范大学学报(自然科学版), 2005, 2005(3): 53-58.

电催化CO₂与有机化合物耦合制备增值化学品

Electrocatalytic coupling of CO₂ with organic compounds to value-added chemicals

RichHTML

PDF

可视化

摘要/Abstract

引用本文

使用本文

图/表 8

参考文献 46

相关文章 2

编辑推荐

Metrics

本文评价