N-Heterocyclic Carbene-Pyridine Manganese Complex/ Tetrabutylammonium Iodide Catalyzed Synthesis of Cyclic Carbonate from CO2 and Epoxide

doi:10.6023/cjoc202206047

Abstract

The bidentate N-heterocyclic carbene (NHC)-pyridine nitrogen manganese complex catalyzed coupling reaction of epoxides with CO₂ was developed. The binary system resulting from the manganese complex Mn-2 in combination with tetrabutylammonium iodide (TBAI) exhibits the high activity for the synthesis of cyclic carbonate from epoxides and CO₂. The binary catalytic system is suitable for a broad range of substrates scope, such as terminal epoxides and sterically hindered internal epoxides. A possible catalytic pathway was elaborated by UV-vis, FT-IR and HRMS method.

Key words: manganese catalysis, carbon dioxide, cyclic carbonate, CO₂ utilization, N-heterocyclic carbene

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Guijie Liu, Zhengqiang Fu, Fei Chen, Caixia Xu, Min Li, Ning Liu. N-Heterocyclic Carbene-Pyridine Manganese Complex/ Tetrabutylammonium Iodide Catalyzed Synthesis of Cyclic Carbonate from CO₂ and Epoxide[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 629-635.

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N-杂环卡宾-吡啶锰配合物/四丁基碘化铵催化CO₂和环氧化物合成环状碳酸酯

N-Heterocyclic Carbene-Pyridine Manganese Complex/ Tetrabutylammonium Iodide Catalyzed Synthesis of Cyclic Carbonate from CO₂ and Epoxide

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Entry	Catalyst (mol%)	Co-catalyst (mol%)	CO₂	T/℃	Time/h	Yield/%
1	Mn-1 (0.15)	TBAB (1.5)	balloon	30	24	31
2	Mn-2 (0.15)	TBAB (1.5)	balloon	30	24	37
3	Mn-3 (0.15)	TBAB (1.5)	balloon	30	24	30
4	Mn-4 (0.15)	TBAB (1.5)	balloon	30	24	18
5	Mn-5 (0.15)	TBAB (1.5)	balloon	30	24	33
6	Mn-2 (0.15)	TBAI (1.5)	balloon	30	24	43
7	Mn-2 (0.15)	TBAC (1.5)	balloon	30	24	34
8	Mn-2 (0.15)	TOAB (1.5)	balloon	30	24	30
9	Mn-2 (0.15)	PPNCl (1.5)	balloon	30	24	38
10	Mn-2 (0.15)	TBAA (1.5)	balloon	30	24	36
11	Mn-2 (0.15)	TOPB (1.5)	balloon	30	24	38
12	Mn-2 (0.3)	TBAI (1.5)	balloon	30	24	60
13	Mn-2 (0.45)	TBAI (1.5)	balloon	30	24	76
14	Mn-2 (0.3)	TBAI (1.5)	0.5 MPa	30	24	64
15	Mn-2 (0.3)	TBAI (1.5)	1.0 MPa	30	24	67
16	Mn-2 (0.3)	TBAI (1.5)	1.0 MPa	40	24	72
17	Mn-2 (0.3)	TBAI (1.5)	1.0 MPa	60	24	79
18	Mn-2 (0.3)	TBAI (1.5)	1.0 MPa	80	12	98
19	Mn-2 (0.3)	TBAI (1.5)	1.0 MPa	80	6	90
20	Mn-2 (0.3)	TBAI (3.0)	1.0 MPa	80	6	92
21	Mn-2 (0)	TBAI (1.5)	1.0 MPa	80	12	40
22	Mn-2 (0.3)	TBAI (0)	1.0 MPa	80	12	0

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N-杂环卡宾-吡啶锰配合物/四丁基碘化铵催化CO2和环氧化物合成环状碳酸酯