CO2插入C—H(sp)键制备丙炔酸衍生物的研究进展

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

摘要/Abstract

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

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

中图分类号:

TQ203.2

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.

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.

图/表 11

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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］

CO₂插入C—H(sp)键制备丙炔酸衍生物的研究进展

Research advances on the carboxylation of terminal alkynes with CO₂

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