Novel System for the Synthesis of Nitriles from Aldehydes Using Aqueous Ammonia and [Bis(Trifluoroacetoxy)iodo]benzene

Abstract

A simple and mild method for the conversion of varieties of aldehydes to the corresponding nitriles using aqueous ammonia and trivalent hypervalent iodine reagent, [bis(trifluoroacetoxy)iodo]benzene, at room temperature is discussed. Advantages of this system are short reaction time, easy workup, and moderate to good yields.

Keywords:

• Aldehydes
• aqueous ammonia
• [bis(trifluoroacetoxy)iodo]benzene
• nitriles

ACKNOWLEDGMENT

We gratefully acknowledge the University Grants Commission, India, for financial support under the scheme of a UGC major research project.

Notes

^a Reaction conditions: substrate (4.5 mmol), [bis(trifluoroacetoxy)iodo]benzene (1.2 equiv, 5.4 mmol), aqueous ammonia (15 mL), rt.

^b Starting compounds were prepared by standard literature procedures.

^c Isolated yields after column chromatography. Structures were confirmed by comparison of IR and ¹H NMR with those of authentic materials.