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

doi:10.6023/cjoc202403024

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (11): 3335-3344.DOI: 10.6023/cjoc202403024 Previous Articles Next Articles

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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

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)

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

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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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Fig. & Tab. 14

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

Figure 2. Structures of complexes 1~4

Figure 3. Structures of complexes 6~16

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]

Table 1. Catalytic hydrogenation of methyl benzoate with different catalysts

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

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

Figure 7. Structures of complexes 17~22

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

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

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

Figure 11. Structures of complexes 24~26

Figure 12. Structures of complexes 27~30

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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Fig. & Tab. 14

References 36

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