腐殖酸作用下Strecker反应快速高效合成α-氨基腈

doi:10.6023/cjoc202301024

摘要/Abstract

以腐殖酸为催化剂, 在室温无溶剂条件下, 通过醛(酮)、胺和三甲基硅氰(TMSCN)的一锅三组分Strecker反应, 绿色高效合成了α-氨基腈. 该法具有产率高、无需金属催化剂、反应时间短、反应条件温和、操作简便以及催化剂绿色并可重复使用等优点.

关键词: Strecker反应, 腐殖酸, 羰基化合物, 胺, α-氨基腈

An efficient one pot three-component Strecker reaction for the green synthesis of α-aminonitriles from carbonyl compounds, amines and trimethylsilyl cyanide (TMSCN) in the presence of a catalytic amount of humic acid catalyst under solvent-free conditions at room temperature has been developed. This methodology has advantages of high yield, no need for metal catalysts, short reaction time, mild reaction conditions, simple operation, green and reusable catalyst.

Key words: Strecker reaction, humic acid, carbonyl compound, amine, α-aminonitrile

引用此文

席敏, 段超, 迟捷, 付甜, 苏小龙, 王宏社. 腐殖酸作用下Strecker反应快速高效合成α-氨基腈[J]. 有机化学, 2023, 43(9): 3312-3318.

Min Xi, Chao Duan, Jie Chi, Tian Fu, Xiaolong Su, Hongshe Wang. An Efficient and Rapid Synthesis of α-Aminonitriles via Strecker Reaction Catalyzed by Humic Acid[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3312-3318.

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Entry	Conditions	Yield/%	Reference
1^a	Mitsunobu's reagent (100 mol%), solvent-free, r.t., 20 min	98	[35]
2	Fe₃O₄ (10 mol%), solvent-free, r.t., 20 min	95	[16]
3	TiCl₃•4H₂O (1 mol%), solvent-free, r.t., 15 min	94	[36]
4	SO₄^2–/ZrO₂ (0.1 g/mmol), THF, r.t., 90 min	93	[37]
5^a	I₂ (10 mol%), CH₃CN, r.t., 1 h	94	[19]
6	Fe₃O₄@SiO₂ core-shell MNP (1 mg/mmol), solvent-free, 50 ℃, 30 min	87	[13]
7	Fe₃O₄@cellulose-OSO₃H (0.04 g/mmol), EtOH, r.t., 15 min	87	[38]
8	Cd(II)-MOF (3 mol%), solvent-free, r.t., 6 h	91	[29f]
9	SmI₃ (10 mol%), THF, r.t., 30 min	98	[27]
10^a	Humic acid (0.1 g/mmol), solvent-free, r.t., 5 min	98	This work

Entry	Conditions	Yield/%	Reference
1^a	Mitsunobu's reagent (100 mol%), solvent-free, r.t., 20 min	98	[35]
2	Fe₃O₄ (10 mol%), solvent-free, r.t., 20 min	95	[16]
3	TiCl₃•4H₂O (1 mol%), solvent-free, r.t., 15 min	94	[36]
4	SO₄^2–/ZrO₂ (0.1 g/mmol), THF, r.t., 90 min	93	[37]
5^a	I₂ (10 mol%), CH₃CN, r.t., 1 h	94	[19]
6	Fe₃O₄@SiO₂ core-shell MNP (1 mg/mmol), solvent-free, 50 ℃, 30 min	87	[13]
7	Fe₃O₄@cellulose-OSO₃H (0.04 g/mmol), EtOH, r.t., 15 min	87	[38]
8	Cd(II)-MOF (3 mol%), solvent-free, r.t., 6 h	91	[29f]
9	SmI₃ (10 mol%), THF, r.t., 30 min	98	[27]
10^a	Humic acid (0.1 g/mmol), solvent-free, r.t., 5 min	98	This work