Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO

Wan-Yin Fang; Hua-Li Qin

doi:10.1021/acs.joc.8b03164

Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH₂OH/Na₂CO₃/SO₂F₂ in DMSO

J Org Chem. 2019 May 3;84(9):5803-5812. doi: 10.1021/acs.joc.8b03164. Epub 2019 Apr 4.

Authors

Wan-Yin Fang¹, Hua-Li Qin¹

Affiliation

¹ State Key Laboratory of Silicate Materials for Architectures and School of Chemistry, Chemical Engineering, and Life Science , Wuhan University of Technology , 205 Luoshi Road , Wuhan 430070 , P. R. China.

PMID: 30868885
DOI: 10.1021/acs.joc.8b03164

Abstract

A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH₂OH/Na₂CO₃/SO₂F₂) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.