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

Molecules

Hashim F. Motiwala²  Qin Yin²  Jeffrey Aubé¹ 

[1] Department of Medicinal Chemistry, Delbert M. Shankel Structural Biology Center, University of Kansas, 2034 Becker Drive, West Campus, Lawrence, KS 66047, USA

关键词: Schmidt reaction;    aldehydes;    nitriles;    HFIP;   

DOI  :  10.3390/molecules21010045

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.