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

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...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 47; no. 23; pp. 3758 - 3766
Main Authors Keita, Massaba, Vandamme, Mathilde, Paquin, Jean-Francois
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.12.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
EFFICIENT HETEROGENEOUS CATALYST
CONVENIENT ACCESS
ENANTIOSELECTIVE SYNTHESIS
ONE-POT SYNTHESIS
aldoximes
PRACTICAL METHOD
amides dehydration
HIGHLY EFFICIENT
ALPHA-AMINONITRILES
nitriles
XtalFluor-E
PROMOTED SYNTHESIS
DEHYDRATION
PRIMARY AMINES
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1378881