Nucleophilic Acylation with Aromatic Aldehydes to 2 Bromoacetonitrile: An Umpolung Strategy for the Synthesis of Active Methylene Compounds.

Current Organic Synthesis
Shailesh SinghJagdamba Singh

Abstract

A novel one-pot N-heterocyclic carbene (NHC)-catalysed acylation of 2- bromoacetonitrile with aromatic aldehydes is reported. The protocol involves carbonyl umpolung reactivity of aldehydes in which the carbonyl carbon attacks nucleophilically (as d1 nucleophile) on the electrophilic terminal of 2-bromoacetonitrile to afford 3-aryl-3-oxopropanenitrile. The salient features of this procedure are short reaction time, operational simplicity, ambient temperature, no by-product formation and high yields. A flame-dried round bottom flask was charged with Imidazolium salts (3a) (0.20 mmol). Aldehyde 1a (1.0 mmol), 2-bromoacetonitrile 2 (1.0 mmol), and THF / t-BuOH 5 mL; 10:1) were added at positive nitrogen pressure followed by the addition of DBU (0.15 mmol) through stirring. The resulting yellow- orange solution was stirred at room temperature for 5-6 h. After completion of the reaction (TLC monitored), the reaction mixture was concentrated under reduced pressure. The product was purified using hexane / EtOAc (10:1) as an eluent to provide analytically pure compound 4a. Physical data of representative compounds and the NMR spectroscopic data are in agreement with the literature value. The salient features of this procedure are short...Continue Reading

References

Nov 4, 2004·Journal of the American Chemical Society·Stephanie S SohnJeffrey W Bode
Nov 6, 2004·The Journal of Organic Chemistry·Lal Dhar S Yadav, Ritu Kapoor
Mar 10, 2006·Organic Letters·Yaohui JiJames V Vowles
Jun 29, 2006·Journal of the American Chemical Society·Ming HeJeffrey W Bode
Jan 8, 2009·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Fawzia Al-QalafAbeer Abdulrahman Bassam
May 17, 2002·Angewandte Chemie·Dieter Enders, Ulrike Kallfass

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