廉价金属配合物应用于均相催化酯加氢制醇的研究进展

doi:10.6023/cjoc202403024

有机化学 ›› 2024, Vol. 44 ›› Issue (11): 3335-3344.DOI: 10.6023/cjoc202403024 上一篇下一篇

综述与进展

廉价金属配合物应用于均相催化酯加氢制醇的研究进展

方霄龙^a^,^*(), 张钰^a, 王韬^a, 李斌^b, 段宁^a, 张峰君^a

a 安徽建筑大学安徽省先进建筑材料工程实验室功能分子设计与界面过程重点实验室合肥 230601
b 湖南师范大学化学化工学院光能转换材料湖南省高校重点实验室长沙 410081

收稿日期:2024-03-19 修回日期:2024-05-07 发布日期:2024-05-30
基金资助:
国家自然科学基金(21802010); 安徽省自然科学基金(2308085MB49); 安徽省优秀青年基金(2023AH030038); 安徽省优秀青年基金(gxyq2022027); 湖南省教育厅重点项目(23A0089); 湖南师范大学测试基金(23CSY016)

Advances in Homogeneous Hydrogenation of Esters to Alcohols by Non-noble Metal Complexes

Xiaolong Fang^a,*(), Yu Zhang^a, Tao Wang^a, Bin Li^b, Ning Duan^a, Fengjun Zhang^a

a Key Laboratory of Functional Molecule Design and Interface Process, Anhui Province Engineering Laboratory of Advanced Building Materials, Anhui Jianzhu University, Hefei 230601
b Key Laboratory of Light Energy Conversion Materials of Hunan Province College, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081

Received:2024-03-19 Revised:2024-05-07 Published:2024-05-30
Contact: *E-mail:xlfang@stu.xmu.edu.cn
Supported by:
National Natural Science Foundation of China(21802010); Anhui Provincial Natural Science Foundation(2308085MB49); Anhui Provincial Fund for Outstanding Young Scholars(2023AH030038); Anhui Provincial Fund for Outstanding Young Scholars(gxyq2022027); Key Program of Hunan Education Committee(23A0089); Measurement Funding of Hunan Normal University(23CSY016)

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摘要/Abstract

酯类分子的催化加氢还原是一种绿色、可持续和原子经济的制备醇类化合物的方法. 近20年来, Ru(II)、Ir(III)、Os(II)等贵金属配合物应用于均相催化酯加氢制醇的研究取得了显著的进展, 将贵金属替代为储量丰富且环境友好的廉价金属已经成为当下的研究热点. 总结了近年来Fe(II)、Co(II)、Mn(I)等廉价金属配合物应用于均相催化酯加氢制醇的研究进展, 围绕配合物结构与性能的关联以及催化加氢反应机理, 探讨了影响配合物性能的关键因素, 为进一步设计开发性能优异的廉价金属配合物催化剂提供参考.

关键词: 廉价金属, 酯, 均相催化加氢, 协同作用

Catalytic hydrogenation of esters to alcohols is a green, sustainable, and atom-economic methodology for alcohol perparation. In the last two decades, the application of noble metal complexes (Ru(II), Ir(III), Os(II), etc.) in homogeneous catalytic hydrogenation of esters to alcohols has achieved significant progress. Replacing noble metals with abundant and environmentally friendly, non-noble metals has been becoming a hot spot. The progress in recent years on the homogeneous catalytic hydrogenation of esters to alcohols is summarized based on non-noble metal complexes including Fe(II), Co(II), and Mn(I). The relationship between complex structure and performance, as well as the catalytic hydrogenation reaction mechanism is detailed discussed to find out the key factors affecting the performance of the complexes, which provides new ideas for further design and development of excellent non-noble metal catalysts.

Key words: non-noble metal, ester, homogeneous catalytic hydrogenation, synergistic effect

引用此文

方霄龙, 张钰, 王韬, 李斌, 段宁, 张峰君. 廉价金属配合物应用于均相催化酯加氢制醇的研究进展[J]. 有机化学, 2024, 44(11): 3335-3344.

Xiaolong Fang, Yu Zhang, Tao Wang, Bin Li, Ning Duan, Fengjun Zhang. Advances in Homogeneous Hydrogenation of Esters to Alcohols by Non-noble Metal Complexes[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3335-3344.

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图/表 14

图1. Ru(II)-NH配合物催化羰基衍生物加氢反应机理

Figure 1. Proposed mechanism for the catalytic hydrogenation of carbonyl derivatives by Ru(II)-NH complex

图2. 配合物1~4的结构

Figure 2. Structures of complexes 1~4

图3. 配合物6~16的结构

Figure 3. Structures of complexes 6~16

图4. 推测的6催化苯甲酸甲酯加氢反应机理

Figure 4. Proposed mechanism for the catalytic hydrogenation of methyl benzoate by 6

Entry	Cat.	Cat./mol%	Temp./℃	p(H₂)/MPa	Time/h	Conv./%	Yield/%	Ref.
1	6	1	60	5.0	6	52	49	[9]
2	7	1	60	3.0	6	99	99	[11]
3	8	2	110	3.0	24	>99	97	[12]
4	9	2	110	2.0	23	>99	97	[12]
5	10	2	120	5.5	20	45	26	[13]
6	11	5	120	5.0	6	>99	99	[14]
7	12	5	140	5.0	48	65	46	[14]
8	13	5	140	5.0	48	67	45	[14]
9	15	0.2	100	5.0	48	—	61	[19]
10	16	1	60	5.0	16	—	97	[20]
11	18	4	130	5.0	48	—	65	[23]
12	19	1	100	2.0	50	99	98	[24]
13	21	0.001	100	10.1	96	—	45	[26]
14	Co(BF₄)₂•6H₂O＋ MeC(CH₂PPh₂)₃	10	100	8.0	5	98	95	[30]
15	24	0.2	100	5.0	16	95	87	[32]
16	24	1	100	5.0	20	99	98	[32]
17	25	1	100	5.0	20	43	24	[32]
18	26	1	100	5.0	20	13	3	[32]
19	30	1	100	5.0	24	96	96	[36]

表1. 系列配合物催化苯甲酸甲酯加氢制苯甲醇反应性能

Table 1. Catalytic hydrogenation of methyl benzoate with different catalysts

图5. 活性物种8b形成过程示意图

Figure 5. Scheme of the formation of active species 8b

图6. 推测的10催化酯加氢反应机理

Figure 6. Proposed mechanism for the catalytic hydrogenation of esters by 10

图7. 配合物17~22的结构

Figure 7. Structures of complexes 17~22

图8. 推测的17催化酯加氢反应机理

Figure 8. Proposed mechanism for the catalytic hydrogenation of esters by 17

图9. 推测的18催化酯加氢反应机理

Figure 9. Proposed mechanism for the catalytic hydrogenation of esters by 18

图10. 推测的23催化酯加氢反应机理

Figure 10. Proposed mechanism for the catalytic hydrogenation of esters by 23

图11. 配合物24~26的结构

Figure 11. Structures of complexes 24~26

图12. 配合物27~30的结构

Figure 12. Structures of complexes 27~30

图13. 推测的27催化酯加氢反应机理

Figure 13. Proposed mechanism for the catalytic hydrogenation of esters by 27

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廉价金属配合物应用于均相催化酯加氢制醇的研究进展

Advances in Homogeneous Hydrogenation of Esters to Alcohols by Non-noble Metal Complexes

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