Synthesis 2015; 47(23): 3758-3766
DOI: 10.1055/s-0034-1378881
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Nitriles from Aldoximes and Primary Amides Using XtalFluor-E

Massaba Keita
CCVC, PROTEO, Canada Research Chair in Organic and Medicinal Chemistry, Département de Chimie, Université Laval, 1045 Avenue de la Médecine, Québec, QC, G1V 0A6, Canada   Email: jean-francois.paquin@chm.ulaval.ca
,
Mathilde Vandamme
CCVC, PROTEO, Canada Research Chair in Organic and Medicinal Chemistry, Département de Chimie, Université Laval, 1045 Avenue de la Médecine, Québec, QC, G1V 0A6, Canada   Email: jean-francois.paquin@chm.ulaval.ca
,
Jean-François Paquin*
CCVC, PROTEO, Canada Research Chair in Organic and Medicinal Chemistry, Département de Chimie, Université Laval, 1045 Avenue de la Médecine, Québec, QC, G1V 0A6, Canada   Email: jean-francois.paquin@chm.ulaval.ca
› Author Affiliations
Further Information

Publication History

Received: 23 June 2015

Accepted after revision: 14 July 2015

Publication Date:
20 August 2015 (online)


Abstract

The dehydration reaction of aldoximes and amides for the synthesis of nitriles using [Et2NSF2]BF4 (XtalFluor-E) is described. Overall, the reaction proceeds rapidly (normally <1 h) at room temperature in an environmentally benign solvent (EtOAc) with only a slight excess of the dehydrating agent (1.1 equiv). A broad scope of nitriles can be prepared, including chiral nonracemic ones. In addition, in a number of cases, further purification of the nitrile after the workup was not required.

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