Research advances on the carboxylation of terminal alkynes with CO2

doi:10.16085/j.issn.1000-6613.2020-1446

Abstract

Abstract:

Propiolic acid compounds are a kind of organic intermediates which are widely used. Using CO₂ as a carboxylation reagent and insert it into the C—H(sp) bond of terminal alkynes is a new route to prepare propiolic acids, which is more environmentally friendly than traditional methods. In this paper, based on systematic analysis of the reaction mechanism, research progress of the catalytic system of the CO₂-based synthesis of propiolic acid was summarized, and some prospective studies closely related to the practical application of the reaction were introduced. Based on the above summary, we think that the following research should be carried out in future works: ①designing the catalyst from the perspective of actual working conditions (resistant to strong alkaline reaction system and strong polar solvent, etc.); ②strengthening the research on reaction mechanism, clarifying the differences on reaction path and intermediate structure for different catalysts, so as to consolidate the theoretical basis; ③seeking to solve potential technical bottlenecks, especially humidity sensitivity, cycling and re-use of the alkali additives, and coupling with downstream synthesis network, etc.

Key words: C—H carboxylation, carbon dioxide, terminal alkynes, propionic acid, catalyst

摘要：

丙炔酸类化合物是一类用途广泛的有机中间体，以CO₂为羧基化试剂，将其插入到端基炔烃的C—H(sp)键是制备丙炔酸类化合物的一条新型路线，其绿色化程度显著高于传统方法。本文在系统分析CO₂路线制备丙炔酸类化合物反应机理的基础上，梳理了该反应催化体系的研究进展，并总结了近年来与该反应实际应用密切相关的前瞻研究。基于上述总结，本文认为后续研究应开展的工作包括：①从实际工况角度（耐强碱性反应体系、耐强极性溶剂等）出发进行催化剂的设计；②强化反应机理研究，明确不同催化剂上的反应路径和中间体形态差异，夯实理论基础；③强化潜在技术瓶颈问题的突破，尤其是湿度敏感、碱助剂循环、下游合成网络衔接等。

关键词: C—H羧酸化, 二氧化碳, 端基炔烃, 丙炔酸, 催化剂

CLC Number:

TQ203.2

LI Minkang, ZHANG Lina, ZHANG Afang, ZHAO Yonghui, SUN Nannan, WEI Wei. Research advances on the carboxylation of terminal alkynes with CO₂[J]. Chemical Industry and Engineering Progress, 2021, 40(6): 3421-3433.

李民康, 张莉娜, 张阿方, 赵永慧, 孙楠楠, 魏伟. CO₂插入C—H(sp)键制备丙炔酸衍生物的研究进展[J]. 化工进展, 2021, 40(6): 3421-3433.

Figures/Tables 11

References 66

1	DECONTO R M, POLLARD D. Contribution of Antarctica to past and future sea-level rise[J]. Nature, 2016, 531(7596): 591-597.
2	CARLETON T A, HSIANG S M. Social and economic impacts of climate[J]. Science, 2016, 353(6304): add9837.
3	IPCC. Climate change 2013: the physical science basis. working group Ⅰ contribution to the fifth assessment report of the intergovernmental panel on climate change[R]. Cambridge: Cambridge University Press, 2013.
4	IEA. World energy outlook 2019[R]. Paris: IEA, 2019.
5	MANJOLINHOHO F, ARANT M, GOOßEN K, et al. Catalytic C—H carboxylation of terminal alkynes with carbon dioxide[J]. ChemInform, 2012, 43(44): 2014-2021.
6	QIAO C, CAO Y, HE L N. Transition metal-catalyzed carboxylation of terminal alkynes with CO₂[J]. Mini-Reviews in Organic Chemistry, 2018, 15: 283-290.
7	YU B, DIAO Z F, GUO C X, et al. Carboxylation of terminal alkynes at ambient CO₂ pressure in ethylene carbonate[J]. Green Chemistry, 2013, 15(9): 2401-2407.
8	GOOßEN L J, RODRÍGUEZ N, MANJOLINHO F, et al. Synthesis of propiolic acids via copper-catalyzed insertion of carbon dioxide into the C—H bond of terminal alkynes[J]. Advanced Synthesis & Catalysis, 2010, 352(17): 2913-2917.
9	LIU C, LUO Y, ZHANG W Z, et al. DFT studies on the silver-catalyzed carboxylation of terminal alkynes with CO₂: an insight into the catalytically activespecies [J]. Organometallics, 2014, 33(12): 2984-2989.
10	YASUO FUKUE S O, INOUE YOSHIO. Direct synthesis of alkyl 2-alkynoates from alklynes, CO₂, and bromoalkanes catalysed by copper(Ⅰ) or silver(Ⅰ) salt[J]. Journal of the Chemical Society, Chemical Communications, 1994, 18: 2091.
11	ZHANG W Z, LI W J, ZHANG X, et al. Cu(Ⅰ)-catalyzed carboxylative coupling of terminal alkynes, allylic chlorides, and CO₂[J]. Organic Letters, 2010, 12(21): 4748-4751.
12	YU D, ZHANG Y. Copper-and copper-N-heterocyclic carbene-catalyzed C—H activating carboxylation of terminal alkynes with CO₂ at ambient conditions[J]. Proceeding of the Royal Society of Sciences of the UnitedStates of America, 2010, 107(47): 20184-20189.
13	DÍAZ VELÁZQUEZ H, WU Z X, VANDICHEL M, et al. Inserting CO₂ into terminal alkynes via bis-(NHC)-metal complexes [J]. Catalysis Letters, 2017, 147(2): 463-471.
14	YUAN Y, CHEN C, ZENG C, et al. Carboxylation of terminal alkynes with carbon dioxide catalyzed by an in situ Ag₂O/N-heterocyclic carbene precursor system [J]. ChemCatChem, 2017, 9(5): 882-887.
15	LI S S, SUN J, ZHANG Z Z, et al. Carboxylation of terminal alkynes with CO₂using novel silver N-heterocyclic carbene complexes[J]. Dalton Transacitions, 2016, 45(26): 10577-10584.
16	ZHANG Z Z, MI R J, GUO F J, et al. 1,3-bis(4-methylbenzyl)imidazol-2-ylidene silver(Ⅰ) chloride catalyzed carboxylative coupling of terminal alkynes, butyl iodide and carbon dioxide[J]. Journal of Saudi Chemical Society, 2017, 21(6): 685-690.
17	WANG W, ZHANG G, LANG R, et al. pH-responsive N-heterocyclic carbene copper(Ⅰ) complexes: syntheses and recoverable applications in the carboxylation of arylboronic esters and benzoxazole with carbon dioxide[J]. Green Chemistry, 2013, 15(3): 635-640.
18	PAPASTAVROU A T, PAUZE M, GÓMEZ BENGOA E, et al. Unprecedented multicomponent organocatalytic synthesis of propargylic esters via CO₂ activation[J]. ChemCatChem, 2019, 11(21): 5379-5386.
19	INAMOTO K, ASANO N, KOBAYASHI K, et al. A copper-based catalytic system for carboxylation of terminal alkynes: synthesis of alkyl 2-alkynoates[J]. Organic & Biomolecular Chemistry, 2012, 10(8): 1514-1516.
20	TRIVEDI M, SINGH G, KUMAR A, et al. 1,1'-bis(di-tert-butylphosphino) ferrocene copper(Ⅰ) complex catalyzed C—H activation and carboxylation of terminal alkynes[J]. Dalton Transactions, 2015, 44(48): 20874-20882.
21	TRIVEDI M, SMREKER J R, SINGH G, et al. Cis-1,2-bis(diphenylphosphino)ethylene copper(Ⅰ) catalyzed C—H activation and carboxylation of terminal alkynes[J]. New Journal of Chemistry, 2017, 41(23): 14145-14151.
22	ZHANG X, ZHANG W Z, REN X, et al. Ligand-free Ag(Ⅰ)-catalyzed carboxylation of terminal alkynes with CO₂[J]. Organic Letters, 2011, 40(5): 2435-2452.
23	ZHANG X, ZHANG W Z, SHI L L, et al. Ligand-free Ag(Ⅰ)-catalyzed carboxylative coupling of terminal alkynes, chloride compounds, and CO₂[J]. Tetrahedron, 2012, 68(44): 9085-9089.
24	LI F W, SUO Q L, HONG H L, et al. DBU and copper(Ⅰ) mediated carboxylation of terminal alkynes using supercritical CO₂ as a reactant and solvent[J]. Tetrahedron Letters, 2014, 55(29): 3878-3880.
25	ARNDT M, RISTO E, KRAUSE T, et al. C—H carboxylation of terminal alkynescatalyzed by low loadings of silver(Ⅰ)/DMSO at ambient CO₂ pressure[J]. ChemCatChem, 2012, 4(4): 484-487.
26	GUO F J, ZHANG Z Z, WANG J Y, et al. Silver-catalyzed one-pot synthesis of benzyl 2-alkynoates under ambient pressure of CO₂ and ligand-free conditions[J]. Tetrahedron, 2017, 73(7): 900-906.
27	WANG W H, JIA L H, FENG X J, et al. Efficient carboxylation of terminal alkynes with carbon dioxide catalyzed by ligand-free copper catalyst under ambient conditions[J]. Asian Journal of Organic Chemistry, 2019, 8(8): 1501-1505.
28	GUO C X, YU B, XIE J N, et al. Silver tungstate: a single-component bifunctional catalyst for carboxylation of terminal alkynes with CO₂ in ambient conditions[J]. Green Chemistry, 2015, 17(1): 474-479.
29	BRESCIANI G, MARCHETTI F, PAMPALONI G. Carboxylation of terminal alkynes promoted by silver carbamate at ambient pressure[J]. New Journal of Chemistry, 2019, 43(27): 10821-10825.
30	YU D Y, TAN M X, ZHANG Y G. Carboxylation of terminal alkynes with carbon dioxide catalyzed by poly(N-heterocyclic carbene)-supported silver nanoparticles[J]. Advanced Synthesis & Catalysis, 2012, 354(6): 969-974.
31	YU B, XIE J N, ZHONG C L, et al. Copper()@carbon-catalyzed carboxylation of terminal alkynes with CO₂ at atmospheric pressure[J]. ACS Catalysis, 2015, 5(7): 3940-3944.
32	LAN X W, LI Y M, DU C, et al. Porous carbon nitride frameworks derived from covalent triazine framework anchored Ag nanoparticles for catalytic CO₂ conversion[J]. Chemistry, 2019, 25(36): 8560-8569.
33	LAN X W, LI Q, CAO L L, et al. Rebuilding supramolecular aggregates to porous hollow N-doped carbon tube inlaid with ultrasmall Ag nanoparticles: a highly efficient catalyst for CO₂ conversion[J]. Applied Surface Science, 2020, 508: 45220-45229.
34	YANG P, ZUO S W, ZHANG F T, et al. Carbon nitride-based single-atom Cu catalysts for highly efficient carboxylation of alkynes with atmospheric CO₂[J]. Industrial & Engineering Chemistry Research, 2020, 59(16): 7327-7335.
35	CHOWDHURY A H, GHOSH S, ISLAM S M. Flower-like AgNPs@ m-MgO as an excellent catalyst for CO₂ fixation and acylation reactions under ambient conditions[J]. New Journal of Chemistry, 2018, 42(17): 14194-14202.
36	ZHANG X, WANG D K, JING M Z, et al. Ordered mesoporous CeO₂-supported Ag as an effective catalyst for carboxylative coupling reaction using CO₂[J]. ChemCatChem, 2019, 11(8): 2089-2098.
37	CHOWDHURY A H, KAYAL U, CHOWDHURY I H, et al. Nanoporous ZnO supported CuBr (CuBr/ZnO): an efficient catalyst for CO₂ fixation reactions[J]. ChemistrySelect, 2019, 4(3): 1069-1077.
38	BONDARENKO G N, DVURECHENSKAYA E G, MAGOMMEDOV E S, et al. Copper(0) nanoparticles supported on Al₂O₃ as catalyst for carboxylation of terminal alkynes[J]. Catalysis Letters, 2017, 147(10): 2570-2580.
39	FINASHINA E D, KUSTOV L M, TKACHENKO O P, et al. Carboxylation of phenylacetylene by carbon dioxide on heterogeneous Ag-containing catalysts[J]. Russian Chemical Bulletin: International Edition, 2014, 63(12): 2652-2656.
40	WU Z L, SUN L, LIU Q G, et al. A Schiff base-modified silver catalyst for efficient fixation of CO₂ as carboxylic acid at ambient pressure[J]. Green Chemistry, 2017, 19(9): 2080-2085.
41	LIU X H, MA J G, NIU Z, et al. An efficient nanoscale heterogeneous catalyst for the capture and conversion of carbon dioxide at ambient pressure[J]. Angewandte Chemie: International Edition, 2015, 54(3): 988-991.
42	ZHU N N, LIU X H, LI T, et al. Composite system of Ag nanoparticles and metal-organic frameworks for the capture and conversion of carbon dioxide under mild conditions[J]. Inorganic Chemistry, 2017, 56(6): 3414-3420.
43	MOLLA R A, GHOSH K, BANERJEE B, et al. Silver nanoparticles embedded over porous metal organic frameworks for carbon dioxide fixation via carboxylation of terminal alkynes at ambient pressure[J]. Journal of Colloid and Interface Science, 2016, 477: 20-29.
44	TRIVEDI M, BHASKARAN B, KUMAR A, et al. Metal-organic framework MIL-101 supported bimetallic Pd-Cu nanocrystals as efficient catalysts for chromium reduction and conversion of carbon dioxide at room temperature[J]. New Journal of Chemistry, 2016, 40(4): 3109-3118.
45	DUTTA G, JANA A K, SINGH D K, et al. Encapsulation of silver nanoparticles in an amine-functionalized porphyrin metal-organic framework and its use as a heterogeneous catalyst for CO₂ fixation under atmospheric pressure[J]. Chemistry—An Asian Journal, 2018, 13(18): 2677-2684.
46	SHI J L, ZHANG L N, SUN N N, et al. Facile and rapid preparation of Ag@ZIF-8 for carboxylation of terminal alkynes with CO₂ in mild conditions[J]. ACS Applied Materials & Interfaces, 2019, 11(32): 28858-28867.
47	GONG Y Y, YUAN Y, CHEN C, et al. Core-shell metal-organic frameworks and metal functionalization to access highest efficiency in catalytic carboxylation[J]. Journal of Catalysis, 2019, 371: 106-115.
48	YUN Y P, SHENG H T, BAO K, et al. Design and remarkable efficiency of the robust sandwich cluster composite nanocatalysts ZIF-8@Au₂₅@ZIF-67[J]. Journal of the American Chemical Society, 2020, 142(9): 4126-4130.
49	XIONG G, YU B, DONG J, et al. Cluster-based MOFs with accelerated chemical conversion of CO₂ through C—C bond formation[J]. Chemical Communications, 2017, 53(44): 6013-6016.
50	GANINA O G, BONDARENKO G N, ISAEVA V I, et al. Cu-MOF-catalyzed carboxylation of alkynes and epoxides[J]. Russian Journal of Organic Chemistry, 2019, 55(12): 1813-1820.
51	WU Z L, LIU Q G, YANG X F, et al. Knitting aryl network polymers-incorporated Ag nanoparticles: a mild and efficient catalyst for the fixation of CO₂ as carboxylic acid[J]. ACS Sustainable Chemistry & Engineering, 2017, 5(11): 9634-9639.
52	LAN X W, DU C, CAO L L, et al. Ultrafine Ag nanoparticles encapsulated by covalent triazine framework nanosheets for CO₂ conversion[J]. ACS Applied Materials & Interfaces, 2018, 10(45): 38953-38962.
53	DANG Q Q, LIU C Y, WANG X M, et al. Novel covalent triazine framework for high-performance CO₂ capture and alkyne carboxylation reaction[J]. ACS Applied Materials & Interfaces, 2018, 10(33): 27972-27978.
54	ZHANG W, MEI Y, HUANG X, et al. Size-controlled growth of silver nanoparticles onto functionalized ordered mesoporous polymers for efficient CO₂ upgrading[J]. ACS Applied Materials & Interfaces, 2019, 11(47): 44241-44248.
55	GHOSH S, GHOSH A, RIYAJUDDIN S, et al. Silver nanoparticles architectured HMP as a recyclable catalyst for tetramic acid and propiolic acid synthesis through CO₂ capture at atmospheric pressure[J]. ChemCatChem, 2020, 12(4): 1055-1067.
56	SALAM N, PAUL P, GHOSH S, et al. AgNPs encapsulated by an amine-functionalized polymer nanocatalyst for CO₂ fixation as a carboxylic acid and the oxidation of cyclohexane under ambient conditions[J]. New Journal of Chemistry, 2020, 44(14): 5448-5456.
57	XIE J N, YU B, ZHOU Z H, et al. Copper(Ⅰ)-based ionic liquid-catalyzed carboxylation of terminal alkynes with CO₂ at atmospheric pressure[J]. Tetrahedron Letters, 2015, 56(50): 7059-7062.
58	CHAUGULE A A, TAMBOLI A H, KIM H. CuCl₂@poly-IL catalyzed carboxylation of terminal alkynes through CO₂ utilization[J]. Chemical Engineering Journal, 2017, 326: 1009-1019.
59	WANG X, LIM Y N, LEE C, et al. 1,5,7-triazabicyclo[4.4.0]dec-1-ene-mediated acetylene dicarboxylation and alkyne carboxylation using carbon dioxide[J]. European Journal of Organic Chemistry, 2013(10): 1867-1871.
60	TONIOLO D, BOBBINK F D, DYSON P J, et al. Anhydrous conditions enable the catalyst-free carboxylation of aromatic alkynes with CO₂ under mild conditions[J]. Helvetica Chimica Acta, 2020, 103(2): e1900258.
61	YU D Y, ZHANG Y G. The direct carboxylation of terminal alkynes with carbon dioxide[J]. Green Chemistry, 2011, 13(5): 1275-1279.
62	WANG W H, FENG X J, SUI K, et al. Transition metal-free carboxylation of terminal alkynes with carbon dioxide through dual activation: synthesis of propiolic acids[J]. Journal of CO₂ Utilization, 2019, 32: 140-145.
63	YU D Y, ZHOU F, LIM D S, et al. NHC-Ag/Pd-catalyzed reductive carboxylation of terminal alkynes with CO₂ and H₂: a combined experimental and computational study for fine-tuned selectivity [J]. ChemSusChem, 2017, 10(5): 836-841.
64	SONG B, HE B Z, QIN A J, et al. Direct polymerization of carbon dioxide, diynes, and alkyl dihalides under mild reaction conditions[J]. Macromolecules, 2017, 51(1): 42-48.
65	KUGE K, LUO Y, FUJITA Y, et al. Copper-catalyzed stereodefined construction of acrylic acid derivatives from terminal alkynes via CO₂ insertion[J]. Organic Letters, 2017, 19(4): 854-857.
66	WENDLING T, RISTO E, KRAUSE T, et al. Salt-free strategy for the insertion of CO₂ into C—H bonds: catalytic hydroxymethylation of alkynes[J]. Chemistry, 2018, 24(23): 6019-6024.

催化剂	温度/℃	压力/MPa	时间/h	收率/%	TON	TOF/h^-1	CTA-D/CTA-E	参考文献
（IPr）CuCl	60	1.5	24	91	9	0.38	CTA-E	［11］
Cu-NHC	25	0.1	16	90	45	2.81	CTA-D	［12］
bis-（NHC）-Ag	室温	0.1	16	85	85	5.31	CTA-D	［13］
L₃/Ag	35	0.1	24	98	392	16.33	CTA-D	［14］
Ag-NHC化合物	室温	0.1	16	82	82	5.13	CTA-D	［15］
Ag-NHC化合物	40	0.1	48	92	46	0.96	CTA-E	［16］
Ag-NHC化合物	60	0.2	12	47	5	0.39	CTA-D	［17］
CuI+PEt₃	室温	0.1	24	90	11	0.47	CTA-E	［19］
［CuI（dtbpf）］	25	0.1	24	96	48	2.00	CTA-D	［20］
［Cu₂（μ-CN）₂（k²-P，P-dppet）₂］	25	0.1	12	97	97	8.08	CTA-D	［21］
AgI	50	0.2	12	94	94	7.83	CTA-D	［22］
AgI	60	1.5	24	91	910	37.92	CTA-E	［23］
CuI	50	8	12	92	46	3.83	CTA-E	［24］
AgBF₄	50	0.1	16	99	1980	123.75	CTA-D	［25］
CuI	80	0.1	18	99	10	0.55	CTA-E	［7］
AgI	40	0.1	48	88	18	0.37	CTA-E	［26］
CuCl	室温	0.1	16	90	18	1.13	CTA-D	［27］
Ag₂WO₄	室温	0.1	24	99	40	1.65	CTA-E	［28］
Ag（O₂CNMe₂）	50	0.1	24	77	39	1.60	CTA-E	［29］

催化剂	温度/℃	压力/MPa	时间/h	收率/%	TON	TOF/h^-1	CTA-D/CTA-E	参考文献
（IPr）CuCl	60	1.5	24	91	9	0.38	CTA-E	［11］
Cu-NHC	25	0.1	16	90	45	2.81	CTA-D	［12］
bis-（NHC）-Ag	室温	0.1	16	85	85	5.31	CTA-D	［13］
L₃/Ag	35	0.1	24	98	392	16.33	CTA-D	［14］
Ag-NHC化合物	室温	0.1	16	82	82	5.13	CTA-D	［15］
Ag-NHC化合物	40	0.1	48	92	46	0.96	CTA-E	［16］
Ag-NHC化合物	60	0.2	12	47	5	0.39	CTA-D	［17］
CuI+PEt₃	室温	0.1	24	90	11	0.47	CTA-E	［19］
［CuI（dtbpf）］	25	0.1	24	96	48	2.00	CTA-D	［20］
［Cu₂（μ-CN）₂（k²-P，P-dppet）₂］	25	0.1	12	97	97	8.08	CTA-D	［21］
AgI	50	0.2	12	94	94	7.83	CTA-D	［22］
AgI	60	1.5	24	91	910	37.92	CTA-E	［23］
CuI	50	8	12	92	46	3.83	CTA-E	［24］
AgBF₄	50	0.1	16	99	1980	123.75	CTA-D	［25］
CuI	80	0.1	18	99	10	0.55	CTA-E	［7］
AgI	40	0.1	48	88	18	0.37	CTA-E	［26］
CuCl	室温	0.1	16	90	18	1.13	CTA-D	［27］
Ag₂WO₄	室温	0.1	24	99	40	1.65	CTA-E	［28］
Ag（O₂CNMe₂）	50	0.1	24	77	39	1.60	CTA-E	［29］

催化剂	温度 /℃	压力 /MPa	时间 /h	收率 /%	TON	TOF /h^-1	CTA-D/CTA-E	参考文献
Ag@P-NHC	25	0.1	20	98	327	16.35	CTA-D	［30］
CuBr@C	80	0.1	2	90	18	9.00	CTA-E	［31］
Ag/PCNF	25	0.1	18	98	71	3.94	CTA-D	［32］
Ag@PHNCT	50	0.1	20	98	94	4.68	CTA-D	［33］
Cu-CN	80	0.1	10	97	97	9.70	CTA-D	［34］
AgNPs@m-MgO	70	0.1	12	98	47	3.89	CTA-D	［36］
Ag/M-CeO₂	60	0.5	24	91	26	1.09	CTA-E	［37］
CuNPs/Al₂O₃	60	0.2	16	92	18	1.15	CTA-E	［38］
Ag/F-Al₂O₃	50	6	18	62	12	0.67	CTA-D	［39］
Ag/Schiff-SiO₂	60	0.1	24	98	705	29.38	CTA-D	［40］

催化剂	温度 /℃	压力 /MPa	时间 /h	收率 /%	TON	TOF /h^-1	CTA-D/CTA-E	参考文献
Ag@P-NHC	25	0.1	20	98	327	16.35	CTA-D	［30］
CuBr@C	80	0.1	2	90	18	9.00	CTA-E	［31］
Ag/PCNF	25	0.1	18	98	71	3.94	CTA-D	［32］
Ag@PHNCT	50	0.1	20	98	94	4.68	CTA-D	［33］
Cu-CN	80	0.1	10	97	97	9.70	CTA-D	［34］
AgNPs@m-MgO	70	0.1	12	98	47	3.89	CTA-D	［36］
Ag/M-CeO₂	60	0.5	24	91	26	1.09	CTA-E	［37］
CuNPs/Al₂O₃	60	0.2	16	92	18	1.15	CTA-E	［38］
Ag/F-Al₂O₃	50	6	18	62	12	0.67	CTA-D	［39］
Ag/Schiff-SiO₂	60	0.1	24	98	705	29.38	CTA-D	［40］

催化剂	温度/℃	压力/MPa	时间/h	收率/%	TON	TOF/h^-1	CTA-D/ CTA-E	参考文献
Ag@MIL-101（Fe）	50	0.1	15	97	36	2.40	CTA-D	［41］
Ag@UIO-66（Zr）	50	0.1	15	96.5	21	1.42	CTA-D	［42］
AgNPs/Co-MOF	80	0.1	14	98	49	3.50	CTA-D	［43］
Pd-Cu/MIL-101	25	0.1	24	96	691	28.79	CTA-D	［44］
Ag@1	60	0.1	6	91	18	3.03	CTA-E	［45］
Ag@ZIF-8	40	0.1	20	97	86	4.31	CTA-D	［46］
UiO-66@UiO-67-BPY-Ag	50	0.1	24	97	80	3.31	CTA-D	［47］
ZIF-8@Au₂₅@ZIF-67	50	0.1	12	99	4433	369.42	CTA-D	［49］
Cu-MOFs	80	0.1	4	80	20	5.00	CTA-E	［50］
Ag/KAPs-P	60	0.1	10	92	9936	993.60	CTA-D	［51］
Ag@CTFN	60	0.1	24	97	128	5.34	CTA-D	［52］
CTF-DCE-Ag	50	0.1	24	90.2	226	9.42	CTA-D	［53］
Ag@NOMP	50	0.1	12	96	960	80.00	CTA-D	［54］
Ag-HMP	80	0.1	12	98	82	6.86	CTA-D	［55］
AgNPs@m-PS-PC	70	0.1	10	91	779	77.93	CTA-D	［56］
［Cu（Im¹²）₂］［CuBr₂］	25	0.1	12	96	10	0.83	CTA-E	［57］
CuCl₂@poly-GLY（1-vim）₃（OMs）₃	40	4	12	96	5	0.40	CTA-E	［58］

Research advances on the carboxylation of terminal alkynes with CO₂

CO₂插入C—H(sp)键制备丙炔酸衍生物的研究进展

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 11

References 66

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	YANG Hanyue, KONG Lingzhen, CHEN Jiaqing, SUN Huan, SONG Jiakai, WANG Sicheng, KONG Biao. Decarbonization performance of downflow tubular gas-liquid contactor of microbubble-type [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 197-204.
[2]	ZHANG Mingyan, LIU Yan, ZHANG Xueting, LIU Yake, LI Congju, ZHANG Xiuling. Research progress of non-noble metal bifunctional catalysts in zinc-air batteries [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 276-286.
[3]	SHI Yongxing, LIN Gang, SUN Xiaohang, JIANG Weigeng, QIAO Dawei, YAN Binhang. Research progress on active sites in Cu-based catalysts for CO₂ hydrogenation to methanol [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 287-298.
[4]	XIE Luyao, CHEN Songzhe, WANG Laijun, ZHANG Ping. Platinum-based catalysts for SO₂ depolarized electrolysis [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 299-309.
[5]	YANG Xiazhen, PENG Yifan, LIU Huazhang, HUO Chao. Regulation of active phase of fused iron catalyst and its catalytic performance of Fischer-Tropsch synthesis [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 310-318.
[6]	ZHENG Qian, GUAN Xiushuai, JIN Shanbiao, ZHANG Changming, ZHANG Xiaochao. Photothermal catalysis synthesis of DMC from CO₂ and methanol over Ce_0.25Zr_0.75O₂ solid solution [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 319-327.
[7]	WANG Lele, YANG Wanrong, YAO Yan, LIU Tao, HE Chuan, LIU Xiao, SU Sheng, KONG Fanhai, ZHU Canghai, XIANG Jun. Influence of spent SCR catalyst blending on the characteristics and deNO _x performance for new SCR catalyst [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 489-497.
[8]	DENG Liping, SHI Haoyu, LIU Xiaolong, CHEN Yaoji, YAN Jingying. Non-noble metal modified vanadium titanium-based catalyst for NH₃-SCR denitrification simultaneous control VOCs [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 542-548.
[9]	SUN Yuyu, CAI Xinlei, TANG Jihai, HUANG Jingjing, HUANG Yiping, LIU Jie. Optimization and energy-saving of a reactive distillation process for the synthesis of methyl methacrylate [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 56-63.
[10]	CHENG Tao, CUI Ruili, SONG Junnan, ZHANG Tianqi, ZHANG Yunhe, LIANG Shijie, PU Shi. Analysis of impurity deposition and pressure drop increase mechanisms in residue hydrotreating unit [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4616-4627.
[11]	WANG Peng, SHI Huibing, ZHAO Deming, FENG Baolin, CHEN Qian, YANG Da. Recent advances on transition metal catalyzed carbonylation of chlorinated compounds [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4649-4666.
[12]	ZHANG Qi, ZHAO Hong, RONG Junfeng. Research progress of anti-toxicity electrocatalysts for oxygen reduction reaction in PEMFC [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4677-4691.
[13]	GE Quanqian, XU Mai, LIANG Xian, WANG Fengwu. Research progress on the application of MOFs in photoelectrocatalysis [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4692-4705.
[14]	WANG Weitao, BAO Tingyu, JIANG Xulu, HE Zhenhong, WANG Kuan, YANG Yang, LIU Zhaotie. Oxidation of benzene to phenol over aldehyde-ketone resin based metal-free catalyst [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4706-4715.
[15]	GE Yafen, SUN Yu, XIAO Peng, LIU Qi, LIU Bo, SUN Chengying, GONG Yanjun. Research progress of zeolite for VOCs removal [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4716-4730.