Cesium Carbonate-Promoted Hydrocyanide Reaction of N-(Quinolin-8-yl)but-3-enamides and Trimethylsilyl Cyanide

doi:10.6023/cjoc202409043

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (7): 2529-2536.DOI: 10.6023/cjoc202409043 Previous Articles Next Articles

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碳酸铯促进N-(8-氨基喹啉)-3-丁烯酰胺与三甲基硅氰的氢氰化反应

朱晓龙, 崔靖, 曾润生^*()

苏州大学材料与化学化工学部江苏苏州 215000

收稿日期:2024-11-23 修回日期:2025-01-19 发布日期:2025-01-24
基金资助:
江苏省前瞻性研究(2020114)

Cesium Carbonate-Promoted Hydrocyanide Reaction of N-(Quinolin-8-yl)but-3-enamides and Trimethylsilyl Cyanide

Xiaolong Zhu, Jing Cui, Runsheng Zeng^*()

College of Chemistry, Chemical Engineering and Materials Science of Scoohow University, Suzhou, Jiangsu 215000

Received:2024-11-23 Revised:2025-01-19 Published:2025-01-24
Contact: *E-mail: zengrunsheng@suda.edu.cn
Supported by:
Prospective Study Program of Jiangsu Province(2020114)

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Abstract

A novel Cs₂CO₃-promoted hydrocyanide reaction of the directing group-protected N-(quinolin-8-yl)but-3-enamides with trimethylsilyl cyanide to afford 3-cyanobutylamides is described. Mechanistic studies have shown that this reaction is a nucleophilic addition reaction of double bonds rather than a free radical reaction.

Key words: olefin, hydrocyanation reaction, cesium carbonate, trimethylsiyl cyanide, 3-cyanobutylamide

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Xiaolong Zhu, Jing Cui, Runsheng Zeng. Cesium Carbonate-Promoted Hydrocyanide Reaction of N-(Quinolin-8-yl)but-3-enamides and Trimethylsilyl Cyanide[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2529-2536.

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Fig. & Tab. 7

References 22

[1]	Yang L.; Ji W.-W.; Lin E.; Li J.-L.; Fan W.-X.; Li Q.; Wang H. Org. Lett. 2018, 20, 1924.
[2]	Wang W.; Ding C.; Li Y.; Li Z.; Li Y.; Peng L.; Yin G. Angew. Chem., Int. Ed. 2019, 58, 4612.
[3]	Han C.; Fu Z.; Guo S.; Fang X.; Lin A.; Yao H. ACS Catal. 2019, 9, 4196.
[4]	Longwitz L.; Werner T. Angew. Chem., Int. Ed. 2020, 59, 2760.
[5]	Song P.; Zhu S. ACS Catal. 2020, 10, 13165.
[6]	Tian T.; Wang X.; Lv L.; Li Z. Chem. Commun. 2020, 56, 14637.
[7]	Hirao Y.; Katayama Y.; Mitsunuma H.; Kanai M. Org. Lett. 2020, 22, 8584. doi: 10.1021/acs.orglett.0c03180 pmid: 33074009
[8]	Liu T.; Yang Y.; Wang Y. Angew. Chem., Int. Ed. 2020, 59, 14256.
[9]	Czyz M. L.; Taylor M. S.; Horngren T. H.; Polyzos A. ACS Catal. 2021, 11, 5472.
[10]	Zhan Y.; Zhao Y.; Du Q.; Rui J.; Chen R.; Zheng X.; Wu X. Green Chem. 2021, 23, 3250.
[11]	Zhang L.-W.; Deng X.-J.; Zhang D.-X.; Tian Q.-Q.; He W. J. Org. Chem. 2021, 86, 5152.
[12]	Simlandy A. K.; Rodphon W.; Alturaifi T. M.; Mai B. K.; Ni H.-Q.; Gurak J. A.; Liu P.; Engle K. M. ACS Catal. 2022, 12, 13755.
[13]	Wu X.; Gannett C. N.; Liu J.; Zeng R.; Novaes L. F. T.; Wang H.; Abruña H. D.; Lin S. J. Am. Chem. Soc. 2022, 144, 17783.
[14]	Yue W. J.; Day C. S.; Rucinski A. B.; Martin R. Org. Lett. 2022, 24, 5109.
[15]	Zhao F.; Xu J.-X.; Wu F.-P.; Wu X.-F. J. Catal. 2023, 417, 379.
[16]	Zhang P. -Z.; Zhang L.; Zou J. -P.; Zhang W. Org. Lett. 2017, 19, 5537.
[17]	Song L.; Fu N.; Ernst B. G.; Lee W.-H.; Frederick M. O.; Lin S. Nat. Chem. 2020, 12, 747. doi: 10.1038/s41557-020-0469-5 pmid: 32601407
[18]	Israr M.; Xiong H.; Li Y.; Bao H. -L. Adv. Synth. Catal. 2020, 362, 2211.
[19]	Li X.-Y.; Tao P.-F.; Huang G.-B. Chin. J. Org. Chem. 2022, 42, 4169 (in Chinese).
	( 李秀英, 陶萍芳, 黄国保, 有机化学, 2022, 42, 4169.) doi: 10.6023/cjoc202204066
[20]	Liu J.-C.; Wan J.-P.; Liu Y.-Y. Org. Chem. Front. 2024, 11, 597.
[21]	Xu Z.; Fu L.; Fang X.; Huang B.; Zhou L.; Wan J.-P. Org. Lett. 2021, 23, 5049.
[22]	Zhang X.-Y.; Geng H.-H.; Zhang S.-L. Chin. J. Org. Chem. 2023, 43, 1510 (in Chinese).
	( 张心予., 耿慧慧, 张士磊, 有机化学, 2023, 43, 1510.) doi: 10.6023/cjoc202210005

Entry	T/℃	Base	Solvent	Yield^b/%
1	60	CsCO₃	CH₃CN	11
2	70	CsCO₃	CH₃CN	39
3	80	CsCO₃	CH₃CN	71
4	90	CsCO₃	CH₃CN	76
5	100	CsCO₃	CH₃CN	69
6	110	CsCO₃	CH₃CN	54
7	90	K₂CO₃	CH₃CN	Trace
8	90	K₂PO₄	CH₃CN	Trace
9	90	Na₂CO₃	CH₃CN	45
10	90	CsCO₃	DMSO	77
11	90	CsCO₃	t-Butanol	23
12	90	CsCO₃	DMF	89
13	90	CsCO₃	Toluene	43

Entry	T/℃	Base	Solvent	Yield^b/%
1	60	CsCO₃	CH₃CN	11
2	70	CsCO₃	CH₃CN	39
3	80	CsCO₃	CH₃CN	71
4	90	CsCO₃	CH₃CN	76
5	100	CsCO₃	CH₃CN	69
6	110	CsCO₃	CH₃CN	54
7	90	K₂CO₃	CH₃CN	Trace
8	90	K₂PO₄	CH₃CN	Trace
9	90	Na₂CO₃	CH₃CN	45
10	90	CsCO₃	DMSO	77
11	90	CsCO₃	t-Butanol	23
12	90	CsCO₃	DMF	89
13	90	CsCO₃	Toluene	43

碳酸铯促进N-(8-氨基喹啉)-3-丁烯酰胺与三甲基硅氰的氢氰化反应

Cesium Carbonate-Promoted Hydrocyanide Reaction of N-(Quinolin-8-yl)but-3-enamides and Trimethylsilyl Cyanide

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