An Efficient and Rapid Synthesis of α-Aminonitriles via Strecker Reaction Catalyzed by Humic Acid

doi:10.6023/cjoc202301024

Abstract

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

Cite this article

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

腐殖酸作用下Strecker反应快速高效合成α-氨基腈