Preparation of Imidazolium Ion Functionalized HG-II Chiral Ruthenium Catalysts and Their Catalytic Performance in Asymmetric Olefin Metathesis

doi:10.6023/cjoc202111029

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1713-1721.DOI: 10.6023/cjoc202111029 Previous Articles Next Articles

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咪唑离子官能化的HG-II型手性钌催化剂的制备及其催化的不对称烯烃复分解反应

李涛^a, 刘艺^a, 白雪^a, 周遵军^a, 左鹏^a, 麻妙锋^a, 仲崇民^a^,^*(), 左亚杰^b^,^*()

a 西北农林科技大学化学与药学院陕西杨凌 712100
b 西北农林科技大学资源环境学院陕西杨凌 712100

收稿日期:2021-11-09 修回日期:2022-01-10 发布日期:2022-03-21
通讯作者: 仲崇民, 左亚杰
基金资助:
国家自然科学基金(21673183)

Preparation of Imidazolium Ion Functionalized HG-II Chiral Ruthenium Catalysts and Their Catalytic Performance in Asymmetric Olefin Metathesis

Tao Li^a, Yi Liu^a, Xue Bai^a, Zunjun Zhou^a, Peng Zuo^a, Miaofeng Ma^a, Chong-Min Zhong^a(), Ya-Jie Zuo^b()

a College of Chemistry and Pharmacy, Northwest Agriculture and Forestry University, Yangling, Shannxi 712100
b College of Natural Resources and Environment, Northwest Agriculture and Forestry University, Yangling, Shannxi 712100

Received:2021-11-09 Revised:2022-01-10 Published:2022-03-21
Contact: Chong-Min Zhong, Ya-Jie Zuo
Supported by:
National Natural Science Foundation of China(21673183)

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Abstract

The yield and stereoselectivity of the ruthenium-catalyzed olefin metathesis reaction are mainly determined by the nature of the ligands. In this study, two chiral HG-II ruthenium catalysts with imidazolium ion functionalized Hoveyda ligands were prepared, and their activity and stereoselectivity in the symmetric ring-closure metathesis (ARCM) and asymmetric ring-opening cross-olefin metathesis (AROCM) reactions were investigated. The results show that the modification of the Hoveyda ligands by ionic functional group produced no significant effect on ARCM reaction. For AROCM reaction, the ionic modification of the Hoveyda ligands shows an obvious improvment on both the E/Z selectivity and ee value for some products. Therefore, in the AROCM reaction, the Hoveyda ligands modified with imidazolium ion can be considered as a means to improve the stereoselectivity of the reaction.

Key words: imidazolium ion, GH-II ruthenium catalysts, chiral ruthenium catalysts, asymmetric ring opening cross metathesis, Hoveyda ligands

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Tao Li, Yi Liu, Xue Bai, Zunjun Zhou, Peng Zuo, Miaofeng Ma, Chong-Min Zhong, Ya-Jie Zuo. Preparation of Imidazolium Ion Functionalized HG-II Chiral Ruthenium Catalysts and Their Catalytic Performance in Asymmetric Olefin Metathesis[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1713-1721.

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Fig. & Tab. 10

References 29

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Entry	Substrate	Product	Catalyst	ee^b/%	Yield^c/%
1	17a	18a	3	11	98
2	17a	18a	1	11	98
3	17b	18b	3	5	94
4	17b	18b	1	3	93
5	17a	18a	4	35	95
6	17a	18a	2	35	96
7	17b	18b	4	40	95
8	17b	18b	2	39	95

Entry	Substrate	Product	Catalyst	ee^b/%	Yield^c/%
1	17a	18a	3	11	98
2	17a	18a	1	11	98
3	17b	18b	3	5	94
4	17b	18b	1	3	93
5	17a	18a	4	35	95
6	17a	18a	2	35	96
7	17b	18b	4	40	95
8	17b	18b	2	39	95

咪唑离子官能化的HG-II型手性钌催化剂的制备及其催化的不对称烯烃复分解反应

Preparation of Imidazolium Ion Functionalized HG-II Chiral Ruthenium Catalysts and Their Catalytic Performance in Asymmetric Olefin Metathesis

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Fig. & Tab. 10

References 29

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Entry	Catalyst	ee^b/%	Yield^c/%	Z∶E^d
1	3	11	98	5∶95
2	1	7	98	23∶77
3	4	21	97	26∶74
4	2	22	97	11∶89
5	3	9	96	5∶95
6	1	15	92	3∶97
7	4	9	95	5∶95
8	2	19	97	2∶98
9	3	65	97	3∶97
10	1	45	98	2∶98
11	4	27	96	2∶98
12	2	50	95	2∶98
13	3	7	97	17∶83
14	1	7	98	17∶83
15	4	27	98	13∶87
16	2	25	96	10∶90

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