Synthesis 2007(21): 3385-3389  
DOI: 10.1055/s-2007-990805
PAPER
© Georg Thieme Verlag Stuttgart · New York

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;
Further Information

Publication History

Received 11 April 2007
Publication Date:
21 September 2007 (online)

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.