title: Improved Schmidt Conversion of Aldehydes to Nitriles Using Azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-propanol.
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.
authors.affiliation: 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.
authors.forename: Hashim F
authors.initials: HF
authors.lastname: Motiwala
authors.affiliation: 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.
authors.forename: Qin
authors.initials: Q
authors.lastname: Yin
authors.affiliation: 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.
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Aubé
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D006860:Hydrogen Bonding; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated
chemical_list: D000447:Aldehydes; D001386:Azides; D020005:Propanols; D012821:Silanes; C438544:azidotrimethylsilane; C001337:hexafluoroisopropanol; D006845:Hydrocarbons, Fluorinated
keywords: HFIP; Schmidt reaction; aldehydes; nitriles