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Molecules 2016, 21(1), 45; doi:10.3390/molecules21010045

Improved Schmidt Conversion of Aldehydes to Nitriles Using Azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-propanol

Department of Medicinal Chemistry, Delbert M. Shankel Structural Biology Center, University of Kansas, 2034 Becker Drive, West Campus, Lawrence, KS 66047, USA
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Academic Editor: Klaus Banert
Received: 5 November 2015 / Revised: 16 December 2015 / Accepted: 22 December 2015 / Published: 29 December 2015
(This article belongs to the Special Issue Organic Azides)
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Abstract

The Schmidt reaction of aromatic aldehydes using a substoichiometric amount (40 mol %) of triflic acid is described. Low catalyst loading was enabled by a strong hydrogen-bond-donating solvent hexafluoro-2-propanol (HFIP). This improved protocol tolerates a broad scope of aldehydes with diverse functional groups and the corresponding nitriles were obtained in good to high yields without the need for aqueous work up. View Full-Text
Keywords: Schmidt reaction; aldehydes; nitriles; HFIP Schmidt reaction; aldehydes; nitriles; HFIP
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Motiwala, H.F.; Yin, Q.; Aubé, J. Improved Schmidt Conversion of Aldehydes to Nitriles Using Azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-propanol. Molecules 2016, 21, 45.

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