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

Hashim F. Motiwala; Qin Yin; Jeffrey Aubé

doi:10.3390/molecules21010045

Molecules (Dec 2015)

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

Hashim F. Motiwala,
Qin Yin,
Jeffrey Aubé

Affiliations

Hashim F. Motiwala: Department of Medicinal Chemistry, Delbert M. Shankel Structural Biology Center, University of Kansas, 2034 Becker Drive, West Campus, Lawrence, KS 66047, USA
Qin Yin: Department of Medicinal Chemistry, Delbert M. Shankel Structural Biology Center, University of Kansas, 2034 Becker Drive, West Campus, Lawrence, KS 66047, USA
Jeffrey Aubé: Department of Medicinal Chemistry, Delbert M. Shankel Structural Biology Center, University of Kansas, 2034 Becker Drive, West Campus, Lawrence, KS 66047, USA

DOI: https://doi.org/10.3390/molecules21010045
Journal volume & issue: Vol. 21, no. 1
p. 45

Abstract

Read online

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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

About the journal

Abstract

Keywords