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

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

Molecules. 2015 Dec 29;21(1):E45. doi: 10.3390/molecules21010045.

Authors

Hashim F Motiwala¹, Qin Yin², Jeffrey Aubé³

Affiliations

¹ Department of Medicinal Chemistry, Delbert M. Shankel Structural Biology Center, University of Kansas, 2034 Becker Drive, West Campus, Lawrence, KS 66047, USA. hashimmotiwala@ku.edu.
² Department of Medicinal Chemistry, Delbert M. Shankel Structural Biology Center, University of Kansas, 2034 Becker Drive, West Campus, Lawrence, KS 66047, USA. qinyin@ku.edu.
³ Department of Medicinal Chemistry, Delbert M. Shankel Structural Biology Center, University of Kansas, 2034 Becker Drive, West Campus, Lawrence, KS 66047, USA. jaube@unc.edu.

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.

Keywords: HFIP; Schmidt reaction; aldehydes; nitriles.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Azides / chemistry*
Catalysis
Hydrogen Bonding
Molecular Structure
Propanols / chemistry*
Silanes / chemistry*

Substances

Aldehydes
Azides
Propanols
Silanes
azidotrimethylsilane
hexafluoroisopropanol