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Synthesis 2015; 47(23): 3758-3766
DOI: 10.1055/s-0034-1378881
DOI: 10.1055/s-0034-1378881
paper
Synthesis of Nitriles from Aldoximes and Primary Amides Using XtalFluor-E
Further Information
Publication History
Received: 23 June 2015
Accepted after revision: 14 July 2015
Publication Date:
20 August 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201523/lookinside/thumbnails/ss-2015-m0394-op_10-1055_s-0034-1378881-1.jpg)
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.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378881.
- Supporting Information
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Selected reviews/books on the use of nitrile-containing molecules in organic synthesis, see:
For other recent selected approaches to nitriles, see:
For recent selected approaches to nitriles from aldoximes, see:
For recent selected approaches to nitriles from primary amides, in addition to references 5b,j,k, see:
For selected examples of chiral nonracemic nitriles obtained from dehydration, see:
For other examples of the synthesis of 16 from 13, see:
For other examples of the synthesis of 17 from 14, see ref. 11c and:
For examples of application of 24 in organic synthesis, see: