Synthesis of N-Arylpyrrolidines Using CO2 as C1 Source

doi:10.6023/cjoc202405042

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (10): 3185-3197.DOI: 10.6023/cjoc202405042 Previous Articles Next Articles

Special Issue: 二氧化碳专题合集

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以CO₂为C1源合成N-芳基吡咯烷

周于佳, 孔荞, 朱道勇^*(), 王少华^*()

兰州大学药学院功能有机分子化学国家重点实验室兰州 730000

收稿日期:2024-05-29 修回日期:2024-08-22 发布日期:2024-09-10
基金资助:
国家重点研发计划(2023YFA1506404); 甘肃省科技计划(23ZDFA003); 甘肃省科技计划(23JRRA1144); 甘肃省科技计划(23JRRA1028); 甘肃省科技计划(23CXGA0043); 兰州市科技计划(2024-1-17); 兰州市科技计划(2023-1-17); 兰州市科技计划(2023-QN-18); 中央高校基本科研业务专项(lzujbky-2022-sp09); 中央高校基本科研业务专项(lzujbky-2023-ct02); 中央高校基本科研业务专项(lzujbky-2023-pd08); 陇药协同创新中心和甘肃省药物研发计(2022GSMPA0010)

Synthesis of N-Arylpyrrolidines Using CO₂ as C1 Source

Yujia Zhou, Qiao Kong, Daoyong Zhu^*(), Shaohua Wang^*()

State Key Laboratory of Applied Organic Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 730000

Received:2024-05-29 Revised:2024-08-22 Published:2024-09-10
Contact: *E-mail: wangshh@lzu.edu.cn;zhudy@lzu.edu.cn
Supported by:
National Key R&D Program of China(2023YFA1506404); Science and Technology Program of Gansu Province(23ZDFA003); Science and Technology Program of Gansu Province(23JRRA1144); Science and Technology Program of Gansu Province(23JRRA1028); Science and Technology Program of Gansu Province(23CXGA0043); Lanzhou Science and Technology Planning Project(2024-1-17); Lanzhou Science and Technology Planning Project(2023-1-17); Lanzhou Science and Technology Planning Project(2023-QN-18); Fundamental Research Funds for the Central Universities(lzujbky-2022-sp09); Fundamental Research Funds for the Central Universities(lzujbky-2023-ct02); Fundamental Research Funds for the Central Universities(lzujbky-2023-pd08); Collaborative Innovation Center for Northwestern Chinese Medicine of Lanzhou University and the Drug Research Project of Gansu Province(2022GSMPA0010)

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Yujia Zhou, Qiao Kong, Daoyong Zhu, Shaohua Wang. Synthesis of N-Arylpyrrolidines Using CO₂ as C1 Source[J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3185-3197.

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Entry	Solvent	Reductant	Catalyst	Base	Yield/%
1	CH₃CN	PhSiH₃	IPr	—	n.d.
2	CH₃CN	PhSiH₃	—	K₂CO₃	n.d.
3	CH₃CN	PhSiH₃	TBD	K₂CO₃	33
4	CH₃CN	PhSiH₃	IPr	K₂CO₃	50
5	CH₃CN	PhSiH₃	DBU	K₂CO₃	17
6	CH₃CN	PhSiH₃	IPr	NaOH	8
7	CH₃CN	PhSiH₃	IPr	DMAP	10
8	CH₃CN	PhSiH₃	IPr	TBD	16
9	CH₃CN	PhSiH₃	IPr	DABCO	60
10	CH₃CN	(EtO)₃SiH	IPr	DABCO	n.d.
11	CH₃CN	Me(EtO)₂SiH	IPr	DABCO	n.d.
12	CH₃CN	PMHS	IPr	DABCO	67
13	CH₃CN	TMCTS	IPr	DABCO	82
14	THF	TMCTS	IPr	DABCO	54
15	DCE	TMCTS	IPr	DABCO	10
16	Butyronitrile	TMCTS	IPr	DABCO	72

Entry	Solvent	Reductant	Catalyst	Base	Yield/%
1	CH₃CN	PhSiH₃	IPr	—	n.d.
2	CH₃CN	PhSiH₃	—	K₂CO₃	n.d.
3	CH₃CN	PhSiH₃	TBD	K₂CO₃	33
4	CH₃CN	PhSiH₃	IPr	K₂CO₃	50
5	CH₃CN	PhSiH₃	DBU	K₂CO₃	17
6	CH₃CN	PhSiH₃	IPr	NaOH	8
7	CH₃CN	PhSiH₃	IPr	DMAP	10
8	CH₃CN	PhSiH₃	IPr	TBD	16
9	CH₃CN	PhSiH₃	IPr	DABCO	60
10	CH₃CN	(EtO)₃SiH	IPr	DABCO	n.d.
11	CH₃CN	Me(EtO)₂SiH	IPr	DABCO	n.d.
12	CH₃CN	PMHS	IPr	DABCO	67
13	CH₃CN	TMCTS	IPr	DABCO	82
14	THF	TMCTS	IPr	DABCO	54
15	DCE	TMCTS	IPr	DABCO	10
16	Butyronitrile	TMCTS	IPr	DABCO	72

Entry	Solvent	Time/h	T/℃	Yield/%
1	CH₃CN	12	r.t	n.d.
2	CH₃CN	12	60	Ttrace
3	CH₃CN	12	80	45
4	CH₃CN	12	100	50
5	CH₃CN	12	120	53
6	CH₃CN	12	140	60
7	CH₃CN	24	140	Trace
8	CH₃CN	16	140	50
9	CH₃CN	10	140	58
10	CH₃CN	8	140	65
11	CH₃CN	6	140	76
12	CH₃CN	6	160	66
13	CH₃CN	4	140	50

Entry	Solvent	Time/h	T/℃	Yield/%
1	CH₃CN	12	r.t	n.d.
2	CH₃CN	12	60	Ttrace
3	CH₃CN	12	80	45
4	CH₃CN	12	100	50
5	CH₃CN	12	120	53
6	CH₃CN	12	140	60
7	CH₃CN	24	140	Trace
8	CH₃CN	16	140	50
9	CH₃CN	10	140	58
10	CH₃CN	8	140	65
11	CH₃CN	6	140	76
12	CH₃CN	6	160	66
13	CH₃CN	4	140	50

以CO₂为C1源合成N-芳基吡咯烷

Synthesis of N-Arylpyrrolidines Using CO₂ as C1 Source

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以CO2为C1源合成N-芳基吡咯烷

Synthesis of N-Arylpyrrolidines Using CO2 as C1 Source

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Supporting Info.

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Abstract

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以CO₂为C1源合成N-芳基吡咯烷

Synthesis of N-Arylpyrrolidines Using CO₂ as C1 Source