One-Pot Microwave-Promoted Synthesis of Nitriles from Aldehydes via tert-Butanesulfinyl Imines

Jessica Tanuwidjaja; Hillary M. Peltier; Jared C. Lewis; Laurie B. Schenkel; Jonathan A. Ellman

doi:10.1055/s-2007-990805

PAPER

One-Pot Microwave-Promoted Synthesis of Nitriles from Aldehydes via tert-Butanesulfinyl Imines

Jessica Tanuwidjaja, Hillary M. Peltier, Jared C. Lewis, Laurie B. Schenkel, Jonathan A. Ellman*
Department of Chemistry, University of California, Berkeley, CA 94720, USA
Fax: +1(510)6428369; e-Mail: jellman@berkeley.edu;

Abstract

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Abstract

A facile, one-pot method for the synthesis of nitriles from aldehydes via a microwave-promoted, concerted elimination of tert-butanesulfenic acid from tert-butanesulfinyl-protected imines, is described. The mild reaction conditions exhibit broad functional group compatibility and generate products in good isolated yield (69-87%). This method provides a rapid and mild procedure for the synthesis of various functionalized nitriles.

Key words

microwave - nitriles - aldehydes - tert-butanesulfinamide - tert-butanesulfinyl imine

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References

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