One-Pot Three-Component Solvent-Free
Cyanoaroylation of Aldehydes Using Potassium Hexacyanoferrate(II)
as an Environmentally Benign Cyanide Source

Zheng Li; Guoqiang Tian; Yuanhong Ma

doi:10.1055/s-0030-1258495

LETTER

One-Pot Three-Component Solvent-Free Cyanoaroylation of Aldehydes Using Potassium Hexacyanoferrate(II) as an Environmentally Benign Cyanide Source

Zheng Li*, Guoqiang Tian, Yuanhong Ma
Key Laboratory of Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China
Fax: +86(931)7971989; e-Mail: lizheng@nwnu.edu.cn;

Abstract

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Abstract

An efficient method for one-pot three-component solvent-free cyanoaroylation of aldehydes using potassium hexacyanoferrate(II) as an environmentally benign cyanide source and triethylamine as a catalyst has been described. This method has advantages of not using strongly toxic cyanating agents and volatile organic solvents. In addition, the product was obtained in high yield using a simple workup procedure.

Key words

aldehydes - cyanohydrins - green chemistry - multicomponent reaction - nucleophilic addition

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References

References and Notes

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General Procedure: To a 50-mL round-bottomed flask equipped with an air condenser, acyl chloride (15 mmol) and potassium hexacyanoferrate(II) (3 mmol) were added. Then the mixture was heated at 160 ˚C for the time indicated in Table [²] . After the resulting mixture was cooled to r.t., aldehyde (15 mmol) and Et₃N (1.5 mmol) were added. The mixture was further stirred for 5-8 min at r.t. The progress of the reaction was monitored by TLC. After completion of the reaction, CH₂Cl₂ (20 mL) was added, and the solid was removed by filtration. The filtrate was then washed with icy H₂O (3 × 30 mL), and dried with anhyd MgSO₄. After removal of the solvent under reduced pressure, the residue was subjected to silica gel flash column chromatography (PE-EtOAc, 20:1) to obtain pure product. The analytical data for the representative products are given below. Cyano(4-methoxyphenyl)methyl Benzoate (Table 2, entry 8): white solid. IR (KBr): 3057, 2250, 1731, 1610, 1514, 1250, 1060, 702 cm^-¹. ^¹H NMR (400 MHz, CDCl₃):
δ = 8.05 (d, J = 6.8 Hz, 2 H), 7.56-7.62 (m, 5 H), 7.25 (d, J = 6.8 Hz, 2 H), 6.65 (s, 1 H), 3.83 (s, 3 H). ^¹³C NMR (100 MHz, CDCl₃): δ = 164.6, 161.1, 133.9, 130.1, 129.6, 128.6, 128.2, 123.9, 116.4, 114.6, 63.1, 55.4. Anal. Calcd for C₁₆H₁₃NO₃: C, 71.90; H, 4.90; N, 5.24. Found: C, 71.96; H, 4.88; N, 5.21.

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Supplementary Material

Supporting Information (PDF)