Amide Functionalized Pyridine/Pyrimidine Chelating N-Heterocyclic Carbene Palladium Complexes: Synthesis, Structure, and Catalysis for C-5 Arylation of Imidazoles

doi:10.6023/cjoc202206005

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (11): 3747-3756.DOI: 10.6023/cjoc202206005 Previous Articles Next Articles

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酰胺功能化吡啶/嘧啶螯合氮杂环卡宾钯化合物的合成、结构及其催化的咪唑C-5芳基化反应

孟祥辉, 杨亮茹^*(), 刘琪琳, 董振华, 袁金伟^*(), 肖咏梅, 毛璞^*()

河南工业大学化学化工学院郑州 450001

收稿日期:2022-06-03 修回日期:2022-07-08 发布日期:2022-07-20
通讯作者: 杨亮茹, 袁金伟, 毛璞
基金资助:
河南省科技厅自然科学基金(212102310332); 河南省留学人员科技活动择优资助; 河南工业大学河南省省属高校基本科研业务费专项基金(2017RCJH08); 河南工业大学创新基金支持计划专项(2020ZKCJ29)

Amide Functionalized Pyridine/Pyrimidine Chelating N-Heterocyclic Carbene Palladium Complexes: Synthesis, Structure, and Catalysis for C-5 Arylation of Imidazoles

Xianghui Meng, Liangru Yang(), Qilin Liu, Zhenhua Dong, Jinwei Yuan(), Yongmei Xiao, Pu Mao()

School of Chemistry & Chemical Engineering, Henan University of Technology, Zhengzhou 450001

Received:2022-06-03 Revised:2022-07-08 Published:2022-07-20
Contact: Liangru Yang, Jinwei Yuan, Pu Mao
Supported by:
Natural Science Foundation of Department of Science and Technology of Henan Province(212102310332); Merit Funding for the Oversea Staff of Henan Province; Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology(2017RCJH08); Innovative Funds Plan of Henan University of Technology(2020ZKCJ29)

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Abstract

A series of N-alkylamide-N'-pyridine/pyrimidine di-functionalized imidazolium salts were synthesized using amino acids as starting material. The following direction metallation with Pd(OAc)₂ in CH₂Cl₂ at room temperature produced chelating N-heterocyclic carbene (NHC) palladium complexes with pyridine/pyrimidine coordinated. The structures have been characterized by nuclear magnetic resonance (NMR), mass spectrum (MS) or elemental analysis (EA). The molecular strucuture of pyridine chelating NHC palladium complex 5c has been further characterized unambiguously by X-ray single crystal analysis. Catalytic activity exploration of the complexes demonstrated their high efficiency towards the C-5 arylation of imidazole derivatives in dimethylacetamide (DMAc) with KOAc as base.

Key words: N-heterocyclic carbene, chelating, palladium complex, arylation of imidazoles

Cite this article

Xianghui Meng, Liangru Yang, Qilin Liu, Zhenhua Dong, Jinwei Yuan, Yongmei Xiao, Pu Mao. Amide Functionalized Pyridine/Pyrimidine Chelating N-Heterocyclic Carbene Palladium Complexes: Synthesis, Structure, and Catalysis for C-5 Arylation of Imidazoles[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3747-3756.

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Fig. & Tab. 6

References 26

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Entry^a	NHC-Pd (mol%)	Yield^b/%
1	5a (2.0)	65
2	5b (2.0)	79
3	5c (2.0)	74
4	5d (2.0)	81
5	5e (2.0)	76
6	5f (2.0)	99
7	5f (1.0)	87
8	C1 (2.0)	55
9	C2 (2.0)	67
10	C3 (2.0)	57
11	C4 (2.0)	89

Entry^a	NHC-Pd (mol%)	Yield^b/%
1	5a (2.0)	65
2	5b (2.0)	79
3	5c (2.0)	74
4	5d (2.0)	81
5	5e (2.0)	76
6	5f (2.0)	99
7	5f (1.0)	87
8	C1 (2.0)	55
9	C2 (2.0)	67
10	C3 (2.0)	57
11	C4 (2.0)	89

Entry ^a	Imidazole	Bromide	Yield^b/%
1	1,2-Dimethylimidazole	p-BrC₆H₄COCH₃	99
2	1,2-Dimethylimidazole	m-BrC₆H₄COCH₃	83
3	1,2-Dimethylimidazole	o-BrC₆H₄COCH₃	0
4	1,2-Dimethylimidazole	p-BrC₆H₄CHO	99
5	1,2-Dimethylimidazole	m-BrC₆H₄CHO	84
6	1,2-Dimethylimidazole	o-BrC₆H₄CHO	70
7	1,2-Dimethylimidazole	p-BrC₆H₄CN	96
8	1,2-Dimethylimidazole	p-BrC₆H₄CH₂CN	74
9	1,2-Dimethylimidazole	p-BrC₆H₄CF₃	91
10	1,2-Dimethylimidazole	p-BrC₆H₄F	90
11	1,2-Dimethylimidazole	C₆H₅Br	66
12	1,2-Dimethylimidazole	p-BrC₆H₄CH₃	54
13	1,2-Dimethylimidazole	m-BrC₆H₄CH₃	51
14	1,2-Dimethylimidazole	o-BrC₆H₄CH₃	0
15	1,2-Dimethylimidazole	p-BrC₆H₄OCH₃	49
16	1,2-Dimethylimidazole	m-BrC₆H₄OCH₃	56
17	1,2-Dimethylimidazole	o-BrC₆H₄OCH₃	0
18	1-Methylimidazole	p-BrC₆H₄COCH₃	92
19	1-Methylimidazole	p-BrC₆H₄CHO	81
21	1-Methylimidazole	m-BrC₆H₄CHO	70
22	1-Methylimidazole	o-BrC₆H₄CHO	46

Entry ^a	Imidazole	Bromide	Yield^b/%
1	1,2-Dimethylimidazole	p-BrC₆H₄COCH₃	99
2	1,2-Dimethylimidazole	m-BrC₆H₄COCH₃	83
3	1,2-Dimethylimidazole	o-BrC₆H₄COCH₃	0
4	1,2-Dimethylimidazole	p-BrC₆H₄CHO	99
5	1,2-Dimethylimidazole	m-BrC₆H₄CHO	84
6	1,2-Dimethylimidazole	o-BrC₆H₄CHO	70
7	1,2-Dimethylimidazole	p-BrC₆H₄CN	96
8	1,2-Dimethylimidazole	p-BrC₆H₄CH₂CN	74
9	1,2-Dimethylimidazole	p-BrC₆H₄CF₃	91
10	1,2-Dimethylimidazole	p-BrC₆H₄F	90
11	1,2-Dimethylimidazole	C₆H₅Br	66
12	1,2-Dimethylimidazole	p-BrC₆H₄CH₃	54
13	1,2-Dimethylimidazole	m-BrC₆H₄CH₃	51
14	1,2-Dimethylimidazole	o-BrC₆H₄CH₃	0
15	1,2-Dimethylimidazole	p-BrC₆H₄OCH₃	49
16	1,2-Dimethylimidazole	m-BrC₆H₄OCH₃	56
17	1,2-Dimethylimidazole	o-BrC₆H₄OCH₃	0
18	1-Methylimidazole	p-BrC₆H₄COCH₃	92
19	1-Methylimidazole	p-BrC₆H₄CHO	81
21	1-Methylimidazole	m-BrC₆H₄CHO	70
22	1-Methylimidazole	o-BrC₆H₄CHO	46

酰胺功能化吡啶/嘧啶螯合氮杂环卡宾钯化合物的合成、结构及其催化的咪唑C-5芳基化反应

Amide Functionalized Pyridine/Pyrimidine Chelating N-Heterocyclic Carbene Palladium Complexes: Synthesis, Structure, and Catalysis for C-5 Arylation of Imidazoles

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Entry^a	Solvent	Base	Temp./℃	Yield^b/%
1	DMAc	KOAc	140	99
2	DMF	KOAc	140	84
3	DMSO	KOAc	140	90
4	Toluene	KOAc	110	65
5	1,4-Dioxane	KOAc	110	0
6	THF	KOAc	60	0
7	DMAc	NaOAc	140	34
8	DMAc	K₂CO₃	140	61
9	DMAc	K₃PO₄•3H₂O	140	55
10	DMAc	K₃PO₄	140	68
11	DMAc	Cs₂CO₃	140	0
12	DMAc	NaH	140	0

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